A modular approach to marine macrolide construction .1. An enantiocontrolled route to the C1-C12 (AB) spiroacetal sector

被引:43
作者
Paquette, LA
Zuev, D
机构
[1] Evans Chemical Laboratories, Ohio State University, Columbus
关键词
D O I
10.1016/S0040-4039(97)01140-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical approach to a desymmetrized, enantiomerically pure AB spiroacetal ring component of altohyrtin A and its congeners is detailed. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5115 / 5118
页数:4
相关论文
共 16 条
[1]   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
[2]   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
[3]  
Kobayashi M, 1996, CHEM PHARM BULL, V44, P2142
[4]  
KOBAYASHI M, 1993, CHEM PHARM BULL, V41, P989
[5]   ABSOLUTE STEREOSTRUCTURES OF ALTOHYRTIN-A AND ITS CONGENERS, POTENT CYTOTOXIC MACROLIDES FROM THE OKINAWAN MARINE SPONGE HYRTIOS-ALTUM [J].
KOBAYASHI, M ;
AOKI, S ;
KITAGAWA, I .
TETRAHEDRON LETTERS, 1994, 35 (08) :1243-1246
[6]   ALTOHYRTIN-A, A POTENT ANTITUMOR MACROLIDE FROM THE OKINAWAN MARINE SPONGE HYRTIOS-ALTUM [J].
KOBAYASHI, M ;
AOKI, S ;
SAKAI, H ;
KAWAZOE, K ;
KIHARA, N ;
SASAKI, T ;
KITAGAWA, I .
TETRAHEDRON LETTERS, 1993, 34 (17) :2795-2798
[7]   NEW C4-CHIRAL 1,3-THIAZOLIDINE-2-THIONES - EXCELLENT CHIRAL AUXILIARIES FOR HIGHLY DIASTEREOCONTROLLED ALDOL-TYPE REACTIONS OF ACETIC-ACID AND ALPHA,BETA-UNSATURATED ALDEHYDES [J].
NAGAO, Y ;
HAGIWARA, Y ;
KUMAGAI, T ;
OCHIAI, M ;
INOUE, T ;
HASHIMOTO, K ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2391-2393
[8]   N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].
NAHM, S ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818
[9]   A MILD METHOD FOR SELECTIVE CLEAVAGE OF TETRAHYDROPYRANYL ETHERS IN THE PRESENCE OF OTHER ACID-LABILE FUNCTIONALITIES [J].
NAMBIAR, KP ;
MITRA, A .
TETRAHEDRON LETTERS, 1994, 35 (19) :3033-3036
[10]   Remote, 1,5-anti stereoinduction in the boron-mediated aldol reactions of beta-oxygenated methyl ketones. [J].
Paterson, I ;
Gibson, KR ;
Oballa, RM .
TETRAHEDRON LETTERS, 1996, 37 (47) :8585-8588