Synlett 2014; 25(09): 1283-1286
DOI: 10.1055/s-0033-1341107
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 7-epi-Goniodiol by Proline-Catalyzed Diastereoselective Direct Aldol Reaction

Bacchu Veena*
D-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Fax: +91(40)27160387   Email: veenabachhu@gmail.com
,
Gangavaram V. M. Sharma
D-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Fax: +91(40)27160387   Email: veenabachhu@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 04 January 2014

Accepted after revision: 13 March 2014

Publication Date:
28 April 2014 (online)


Abstract

A simple organocatalytic approach was developed for the total synthesis of 7-epi-goniodiol. The strategy involves l-proline-catalyzed diastereoselective direct aldol reaction and Baeyer–Villiger oxidation as key steps for the construction of chiral lactone.

Supporting Information

 
  • References

    • 1a Wu YC, Duh CY, Chang FR, Wang SK, Chang JJ, McPhail DR, McPhail AT, Lee KH. J. Nat. Prod. 1991; 54: 1077
    • 1b Sam TW, Saw-Yeu C, Matsjeh S, Gan EK, Razak D, Mohamed AL. Tetrahedron Lett. 1987; 28: 2541
    • 1c Talapatra SK, Basu D, Goaiwami S, Talapatra B. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985; 24: 29
    • 1d Fang XP, Anderson JE, Qui XX, Kozlowski JF, McLaughlin JL. Tetrahedron 1993; 49: 1563
    • 1e Fang XP, Anderson JE, Chang CJ, McLaughlin JL. J. Nat. Prod. 1991; 54: 1034
    • 2a Mereyala HB, Joe M. Curr. Med. Chem.: Anti-Cancer Agents 2001; 1: 293
    • 2b Muhammad Z, Saito I, Matsuura TC. Int. J. Crude Drug Res. 1989; 27: 92
    • 2c Ahmad FB, Tukol WA, Omar S, Sharif AM. Phytochemistry 1991; 30: 2430
    • 2d Hasan CM, Hussain MA, Mia MY, Rashid MA. Fitoterapia 1995; 66: 378
    • 3a Mu Q, Tang WD, Liu RY, Li CM, Lou LG, Sun HD. Planta Med. 2003; 69: 826
    • 3b Pihie AH, Stanslas J, Din LB. Anticancer Res. 1998; 18: 1739
    • 4a Mu Q, Li CM, He YN, Sun HD, Zheng HL, Lu Y, Zheng QT, Jiang RW. Chin. Chem. Lett. 1999; 10: 135
    • 4b Mu Q, Tang W, Li C, Lu Y, Sun H, Zheng X, Wu N, Lou B, Xu B. Heterocycles 1999; 51: 2969
    • 5a List B, Pojarliev P, Castello C. Org. Lett. 2001; 3: 573
    • 5b Sun B, Peng L, Chen X, Li Y, Li Y, Yamasaki K. Tetrahedron: Asymmetry 2005; 16: 1305
    • 5c Ikishima H, Sekiguchi Y, Ichikawa Y, Kotsuki H. Tetrahedron 2006; 62: 311
  • 6 Atobe M, Yamazaki N, Kibayashi C. J. Org. Chem. 2004; 69: 5595
  • 7 Takahiro Y, Satoshi Y, Ryosuke T, Masafumi M, Koichi A, Takuya S, Taro K, Yojiro K. Biosci. Biotechnol. Biochem. 2008; 72: 2342
  • 8 Prasad KR, Gholap SL. Tetrahedron Lett. 2007; 48: 4679