A modular approach to marine macrolide construction .2. Concise stereocontrolled synthesis of the C17-C28 (CD) spiroacetal component

被引:47
作者
Paquette, LA
Braun, A
机构
[1] Evans Chemical Laboratories, Ohio State University, Columbus
关键词
D O I
10.1016/S0040-4039(97)01141-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The CD spiroacetal ring system of altohyrtin A, which houses one-fifth of the stereogenic centers resident in the macrolide, has been synthesized through a combination of aldol condensations having different stereocontrol elements. (C) 1997 Elsevier Science Ltd.
引用
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页码:5119 / 5122
页数:4
相关论文
共 25 条
[1]  
[Anonymous], 1994, Org. React
[2]   SYNTHESIS OF BRYOSTATINS .1. CONSTRUCTION OF THE C(1)-C(16) FRAGMENT [J].
BLANCHETTE, MA ;
MALAMAS, MS ;
NANTZ, MH ;
ROBERTS, JC ;
SOMFAI, P ;
WHRITENOUR, DC ;
MASAMUNE, S ;
KAGEYAMA, M ;
TAMURA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2817-2825
[3]   VINYL ETHER HYDROLYSIS .19. 1-METHOXY-1,3-BUTADIENE - REACTION-MECHANISM AND IMPLICATION FOR HYDROLYSIS OF THE MUTAGEN FECAPENTAENE-12 [J].
CHIANG, Y ;
ELIASON, R ;
GUO, GHX ;
KRESGE, AJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (07) :1632-1636
[4]   A method for constructing the C2-C12 dispiroacetal moiety of altohyrtin A [J].
Claffey, MM ;
Heathcock, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7646-7647
[5]   A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes [J].
Evans, DA ;
Dart, MJ ;
Duffy, JL ;
Yang, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4322-4343
[6]   1,3-ASYMMETRIC INDUCTION IN THE ALDOL ADDITION-REACTIONS OF METHYL KETONE ENOLATES AND ENOLSILANES TO BETA-SUBSTITUTED ALDEHYDES - A MODEL FOR CHIRALITY TRANSFER [J].
EVANS, DA ;
DUFFY, JL ;
DART, MJ .
TETRAHEDRON LETTERS, 1994, 35 (46) :8537-8540
[7]   1,5-asymmetric induction in methyl ketone aldol addition reactions [J].
Evans, DA ;
Coleman, PJ ;
Cote, B .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :788-789
[8]  
FUJITA E, 1989, ADV HETEROCYCL CHEM, P1
[9]   BIOACTIVE MARINE METABOLITES .48. CINACHYROLIDE-A - A POTENT CYTOTOXIC MACROLIDE POSSESSING 2 SPIRO KETALS FROM MARINE SPONGE CINACHYRA SP [J].
FUSETANI, N ;
SHIMODA, K ;
MATSUNAGA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3977-3981
[10]   An efficient synthesis of C-20-C-25 building blocks for calyculin A [J].
Hamada, Y ;
Yokokawa, F ;
Kabeya, M ;
Hatano, K ;
Kurono, Y ;
Shioiri, T .
TETRAHEDRON, 1996, 52 (24) :8297-8306