Concise Asymmetric Synthesis of Deepoxyalchornoic Acid and (12R,13R)-Isoleukotoxin Diol

Abstract

The first asymmetric synthesis and structural confirmation of deepoxyalchornoic acid have been accomplished from commercially available starting materials. Asymmetric dihydroxylation and Wittig olefination has been strategically executed to achieve a concise synthesis of deepoxyalchornoic acid and (12R,13R)-isoleukotoxin diol from a common intermediate chiral γ-lactone.

Key words

deepoxyalchornoic acid - (12R,13R)-isoleukotoxin diol - lactone - asymmetric dihydroxylation - Wittig olefination - natural product

Publikationsverlauf

Eingereicht: 09. Juli 2024

Angenommen nach Revision: 07. August 2024

Accepted Manuscript online:
07. August 2024

Artikel online veröffentlicht:
19. September 2024

• References

• 1 Mosblech A, Feussner I, Heilmann I. Plant Physiol. Biochem. 2009; 47: 511
• 2a Liu C, Liu F, Cai J, Xie W, Long TE, Turner SR, Lyons A, Gross RA. Biomacromolecules 2011; 12: 3291
• 2b Nanda S, Patra BR, Patel R, Bakos J, Dalai AK. Environ. Chem. Lett. 2022; 20: 379
• 3a Hou CT. New Biotechnol. 2009; 26: 2
• 3b Cooper DG, Zajic JE, Denis C. J. Am. Oil Chem. Soc. 1981; 58: 77
• 3c Oh HJ, Kim SU, Song JW, Lee JH, Kang WR, Jo YS, Kim KR, Bornscheuer UT, Oh DK, Park JB. Adv. Synth. Catal. 2015; 357: 408
• 4 Knothe G, Dunn RO, Bagby MO. J. Am. Oil Chem. Soc. 1995; 72: 43
• 5 Hou CT. Asia Pac. J. Clin. Nutr. 2008; 17 (Suppl. 01) 192
• 6 Ebessa V, Laure G, Tiani M, Tchamgoue J, Kouam SF, Ngadjui BT, Green IR, Choudhary MI, Tane P. Phytochem. Lett. 2018; 23: 62
• 7 Wu ZY. Acta Bot. Yunnan 1991; 4: 1
• 8 Sevanian A, Mead JF, Stein RA. Lipids 1979; 14: 634
• 9a Markaverich BM, Crowley JR, Alejandro MA, Shoulars K, Casajuna N, Mani S, Reyna A, Sharp J. Environ. Health Perspect. 2005; 113: 1698
• 9b Markaverich BM, Alejandro M, Thompson T, Mani S, Reyna A, Portillo W, Sharp J, Turk J, Crowley JR. Environ. Health Perspect. 2007; 115: 702
• 10 Nanba Y, Shinohara R, Morita M, Kobayashi Y. Org. Biomol. Chem. 2017; 15: 8614
• 11a Yamanaka H, Yokoyama M, Sakamoto T, Shiraishi T, Sagi M, Mizugaki M. Heterocycles 1983; 20: 1541
• 11b Ragoussis N. Tetrahedron Lett. 1987; 28: 93
• 11c Halle MB, Fernandes RA. RSC Adv. 2014; 4: 63342
• 12a Braukmüller S, Brückner R. Eur. J. Org. Chem. 2006; 2110
• 12b Takahata H, Uchida Y, Momose T. J. Org. Chem. 1995; 60: 5628
• 12c García C, Martín T, Martín VS. J. Org. Chem. 2001; 66: 1420
• 13 Dawson MI, Vasser M. J. Org. Chem. 1977; 42: 2783
• 14 For a similar reaction, see: Kumari A, Gholap SP, Fernandes RA. Chem. Asian J. 2019;  14: 2278
• 15 For a similar reaction, see: Thurnhofer S, Vetter W. Tetrahedron 2007; 63: 1140
• 16a Thomas M. J. Am. Oil Chem. Soc. 1971; 48: 259
• 16b Kikukawa H, Sakuradani E, Nishibaba Y, Okuda T, Ando A, Shima J, Shimizu S, Ogawa J. J. Appl. Microbiol. 2014; 118: 641