Synthesis of (+)-prelactone B

被引:38
作者
Chakraborty, TK [1 ]
Tapadar, S [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
prelactone B; sharpless kinetic resolution; epoxide opening; 2-methyl-1,3-diol;
D O I
10.1016/S0040-4039(03)00326-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radical-mediated opening of a trisubstituted epoxy alcohol using cp(2)TiCl was followed by diastereoselective reduction of the resulting product with a centrally located methylene group, flanked on both sides by two chiral hydroxyl-bearing carbons, to build all the three chiral centers of (+)-prelactone B 1 in their desired stereochemistries leading to the total synthesis of the molecule. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2541 / 2543
页数:3
相关论文
共 12 条
[1]   A new strategy for the synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes [J].
Barrero, AF ;
Cuerva, JM ;
Herrador, MM ;
Valdivia, MV .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4074-4078
[2]   METABOLIC PRODUCTS OF MICROORGANISMS .265. PRELACTONE-C AND PRELACTONE-B, OLIGOKETIDES FROM STREPTOMYCES PRODUCING CONCANAMYCINS AND BAFILOMYCINS [J].
BINDSEIL, KU ;
ZEECK, A .
HELVETICA CHIMICA ACTA, 1993, 76 (01) :150-157
[3]   Synthesis of chiral 1,3-diols by radical-mediated regioselective opening of 2,3-epoxy alcohols using cp2TiCl [J].
Chakraborty, TK ;
Das, S .
TETRAHEDRON LETTERS, 2002, 43 (12) :2313-2315
[4]   Anti-Markovnikov opening of trisubstituted epoxy alcohols: application in the synthesis of 2-methyl-1,3-diols [J].
Chakraborty, TK ;
Dutta, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1257-1259
[5]   Radical-induced opening of trisubstituted epoxides:: Application in the synthesis of C1-C12 segment of epothilones [J].
Chakraborty, TK ;
Dutta, S .
TETRAHEDRON LETTERS, 1998, 39 (1-2) :101-104
[6]  
CHAKRABORTY TK, 2001, J INDIAN CHEM SOC, V78, P45
[7]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[8]  
Hanefeld U, 1999, SYNTHESIS-STUTTGART, P401
[9]   Tolerance and specificity of polyketide synthases [J].
Khosla, C ;
Gokhale, RS ;
Jacobsen, JR ;
Cane, DE .
ANNUAL REVIEW OF BIOCHEMISTRY, 1999, 68 :219-253
[10]  
OHAGEN D, 1991, POLYKETIDE METABOLIT, P116