A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols

Abstract

Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation–oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.

Key words

oxa-[3+3] annulation - resorcinol - bioinspired total synthesis - (±)-daurichromenic acid - (±)-rhododaurichromanic acid A

• References


For reviews on oxa-[3+3] annulations, see:
• 1a Harrity JP. A, Provoost O. Org. Biomol. Chem. 2005; 3: 1349
• 1b Hsung RP, Kurdyumov AV, Sydorenko N. Eur. J. Org. Chem. 2005; 23
• 1c Hsung RP, Cole KP. Strategies and Tactics in Organic Synthesis . Pergamon; Oxford: 2004: 41
• 1d Deng J, Wang X.-N, Hsung RP. A Formal [3+3] Cycloaddition Approach to Natural Product Synthesis. In Methods and Applications of Cycloaddition Reactions in Organic Syntheses. Nishiwaki N. Wiley-VCH; Weinheim: 2014. Chap. 12

For recent reviews on [3+3] cycloadditions, see:
• 2a Xu X, Doyle MP. Acc. Chem. Res. 2014; 47: 1396
• 2b Moyano A, Rios R. Chem. Rev. 2011; 111: 4703

For recent development and applications employing oxa-[3+3] annulations, see:
• 3a Fotiadou AD, Zografos AL. Org. Lett. 2012; 14: 5664
• 3b Hu J, Dong W, Wu X.-Y, Tong X. Org. Lett. 2012; 14: 5530
• 3c dos Santos WH, da Silva-Filho LC. Synthesis 2012; 44: 3361
• 3d Lee YR, Pandit RP. Synthesis 2012; 44: 2910
• 3e Parker KA, Thomas L, Mindt TL. Tetrahedron 2011; 67: 9779

For applications in total syntheses, see:
• 4a Song L, Yao H, Zhu L, Tong R. Org. Lett. 2013; 15: 6
• 4b Buchanan GS, Cole KP, Tang Y, Hsung RP. J. Org. Chem. 2011; 76: 7027
• 4c Buchanan GS, Cole KP, Li G, Tang Y, You L, Hsung RP. Tetrahedron 2011; 67: 10105
• 4d Yamashita S, Iso K, Kitajima K, Himura M, Hirama M. J. Org. Chem. 2011; 76: 2408
• 5 For a leading review, see: Tang Y, Oppenheimer J, Song Z, You L, Zhang X, Hsung RP. Tetrahedron 2006; 62: 10785

For leading reviews, see:
• 6a Tietze LF. Chem. Rev. 1996; 96: 115
• 6b Tietze LF, Beifuss U. Angew. Chem., Int. Ed. Engl. 1993; 32: 131
• 6c Tietze LF. J. Heterocycl. Chem. 1990; 27: 47
• 7 For a recent review on biomimetic synthesis, see: Bulger PG, Bagal SK, Marquez R. Nat. Prod. Rep. 2008; 25: 254

See also:
• 8a Yoder RA, Johnston JN. Chem. Rev. 2005; 105: 4730
• 8b Beaudry CM, Malerich JP, Trauner D. Chem. Rev. 2005; 105: 4757
• 8c Pindur U, Schneider GH. Chem. Soc. Rev. 1994; 23: 409
• 9 Shen HC, Wang J, Cole KP, McLaughlin MJ, Morgan CD, Douglas CJ, Hsung RP, Coverdale HA, Gerasyuto AI, Hahn JM, Liu J, Wei L.-L, Sklenicka HM, Zehnder LR, Zificsak CA. J. Org. Chem. 2003; 68: 1729

For some earlier studies, see:
• 10a Stevenson R, Weber JV. J. Nat. Prod. 1988; 51: 1215
• 10b Schuda PF, Price WA. J. Org. Chem. 1987; 52: 1972
• 10c de March P, Moreno-Mañas M, Casado J, Pleixats R, Roca JL. J. Heterocycl. Chem. 1984; 21: 85
• 10d Tietze LF, Kiedrowski GV, Berger B. Synthesis 1982; 683
• 11 For a leading review, see: Shen HC. Tetrahedron 2009; 65: 3931
• 12 Kang Y, Mei Y, Du Y, Jin Z. Org. Lett. 2003; 5: 4481
• 13a Wang X, Lee YR. Tetrahedron 2011; 67: 9179 ; and references cited therein
• 13b Jung EJ, Park BH, Lee YR. Green Chem. 2010; 12: 2003
• 13c Wang X, Lee YR. Tetrahedron 2009; 65: 10125
• 14a Mondal M, Puranik VG, Argade NP. J. Org. Chem. 2007; 72: 2068
• 14b See also: Zeng H, Duan D, Tang B. Synlett 2015; 26: 927
• 15 Yeom H.-S, Li H, Tang Y, Hsung RP. Org. Lett. 2013; 15: 3130
• 16 Hua DH, Chen Y, Sin H.-S, Maroto MJ, Robinson PD, Newell SW, Perchellet EM, Ladesich JB, Freeman JA, Perchellet J.-P, Chiang PK. J. Org. Chem. 1997; 62: 6888
• 17a Wei L.-L, Hsung RP, Sklenicka HM, Gerasyuto AI. Angew. Chem. Int. Ed. 2001; 40: 1516
• 17b Sklenicka HM, Hsung RP, McLaughlin MJ, Wei L.-L, Gerasyuto AI, Brennessel WW. J. Am. Chem. Soc. 2002; 124: 10435
• 18a Gerasyuto AI, Hsung RP, Sydorenko N, Slafer BW. J. Org. Chem. 2005; 70: 4248
• 18b Cravotto G, Nano GM, Tagliapietra S. Synthesis 2001; 49
• 19 Hsung RP, Shen HC, Douglas CJ, Morgan CD, Degen SJ, Yao LJ. J. Org. Chem. 1999; 64: 690
• 20a For a related condensation using ethylenediamine acetate salt that led to cannabichromeme, see: Lee YR, Wang X. Bull. Korean Chem. Soc. 2005; 26: 1933
• 20b See also: Mechoulam R, Yapnitinsky B, Gaoni Y. J. Am. Chem. Soc. 1968; 90: 2420
• 21 Murrayamine M, Wu T.-S, Wang M.-L, Wu P.-L, Ito C, Furukawa H. Phytochemistry 1996; 41: 1433
• 22a Kurdyumov AV, Lin N, Hsung RP, Gullickson GC, Cole KP, Sydorenko N, Swidorski JJ. Org. Lett. 2006; 8: 191
• 22b Sagar R, Singh P, Kumar R, Maulik PR, Shaw AK. Carbohydr. Res. 2005; 340: 1287
• 22c Lee YR, Kim DH, Shim J.-J, Kim SK, Park JH, Cha JS, Lee C.-S. Bull. Korean Chem. Soc. 2002; 23: 998
• 23 Zehnder LR, Dahl JW, Hsung RP. Tetrahedron Lett. 2000; 41: 1901
• 24 Melliou E, Magiatis P, Mitaku S, Skaltsounis A.-L, Chinou E, Chinou I. J. Nat. Prod. 2005; 68: 78

For isolation of eriobrucinol, see:
• 25a Jefferies PR, Worth GK. Tetrahedron 1973; 29: 903
• 25b Bukuru J, Van TN, Puyvelde LV, He W, De Kimpe N. Tetrahedron 2003; 59: 5905
• 25c For additional data on eriobrucinol, see: Rashid MA, Armstrong JA, Gray AI, Waterman PG. Phytochemistry 1992; 31: 3583

For total syntheses of iso-eriobrucinol A and B, and eriobrucinol, see:
• 26a Crombie L, Redshaw SD, Black DA, Whiting DA. J. Chem. Soc., Chem. Commun. 1979; 628
• 26b Crombie L, Redshaw SD, Black DA, Whiting DA. J. Chem. Soc., Perkin Trans. 1 1983; 1411
• 27a Gassman PG, Chavan SP, Fertel LB. Tetrahedron Lett. 1990; 31: 6489
• 27b Gassman PG, Lottes AC. Tetrahedron Lett. 1992; 33: 157
• 28a Ko C, Feltenberger JB, Ghosh SK, Hsung RP. Org. Lett. 2008; 10: 1971
• 28b Feltenberger JB, Ko C, Deng J, Ghosh SK, Hsung RP. Heterocycles 2012; 84: 843
• 28c Deng J, Hsung RP, Ko C. Org. Lett. 2012; 14: 5562
• 29 Jpn. Kokai Tokyo Koho JP 82-28080, 1982 ; Chem. Abstr. 1982, 97, 3777.
• 30 For isolation, see: Kashiwada Y, Yamazaki K, Ikeshiro Y, Yamagishi T, Fujioka T, Mihashi K, Mizuki K, Cosentino LM, Fowke K, Morris-Natschke SL, Lee K.-H. Tetrahedron 2001; 57: 1559

For total syntheses, see:
• 31a Kurdyumov AV, Hsung RP, Ihlen K, Wang J. Org. Lett. 2003; 5: 3935
• 31b Hu H, Harrison TJ, Wilson PD. J. Org. Chem. 2004; 69: 3782
• 31c See also: Ref. 12.
• 32 Kurdyumov AV, Hsung RP. J. Am. Chem. Soc. 2006; 128: 6272
• 33a Roll DM, Manning JK, Carter GT. J. Antibiot. 1998; 51: 635
• 33b For fermentation studies, see: Abbanat DA, Singh MP, Greenstein M. J. Antibiot. 1998; 51: 708

For an earlier total synthesis of hongoquercin A, see:
• 34a Tsujimori H, Bando M, Mori K. Eur. J. Org. Chem. 2000; 297
• 34b Tsujimori H, Mori K. Biosci. Biotechnol. Biochem. 2000; 64: 1410