TOTAL SYNTHESIS OF (+)-MONOMORINE-I VIA NITRONE CYCLOADDITION ROUTE

被引：50

作者：

ITO, M ^{[1
]}

KIBAYASHI, C ^{[1
]}

机构：

[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 45期

关键词：

NITRONE; 1,3-DIPOLAR CYCLOADDITION; CHIRAL ALLYLIC ETHER; INSIDE ALKOXY EFFECT; (+)-MONOMORINE-I;

D O I：

10.1016/S0040-4020(01)80881-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective total synthesis of (+)-monomorine I (1) is described. The key feature of the synthesis is the asymmetric 1,3-dipolar cycloaddition of the prochiral nitrone 9 with the chiral (S)-allylic ether 8 as a dipolarophile, which provides stereoselectively the C-3,C-5-trans-isoxazolidine 10 with the correct relative and absolute stereochemistry suitable for the synthesis of (+)-monomorine I.

引用

页码：9329 / 9350

页数：22

共 79 条

[71] TOTAL SYNTHESIS OF (+/-)-DIHYDROPINIDINE, (+/-)-MONOMORINE-I, AND (+/-)-INDOLIZIDINE-223AB (GEPHYROTOXIN-223AB) BY INTRAMOLECULAR NITROSO DIELS-ALDER REACTION
WATANABE, Y
IIDA, H
KIBAYASHI, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) : 4088 - 4097
[72] STRUCTURE, SYNTHESIS AND ABSOLUTE-CONFIGURATION OF LEPTOSPHAERIN, A METABOLITE OF THE MARINE ASCOMYCETE LEPTOSPHAERIA-ORAEMARIS
WHITE, JD
BADGER, RA
KEZAR, HS
PALLENBERG, AJ
SCHIEHSER, GA
[J]. TETRAHEDRON, 1989, 45 (21) : 6631 - 6644
[73] A 1,3-DIPOLAR CYCLOADDITION ROUTE TO THE 3(R)-HYDROXY-(2S)-ARGININES AND 3(S)-HYDROXY-(2S)-ARGININES
WITYAK, J
GOULD, SJ
HEIN, SJ
KESZLER, DA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) : 2179 - 2183
[74] A CHIRAL SYNTHESIS OF L-ACOSAMINE AND L-DAUNOSAMINE VIA AN ENANTIOSELECTIVE INTRAMOLECULAR [3+2] CYCLOADDITION
WOVKULICH, PM
USKOKOVIC, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) : 3956 - 3958
[75] STEREOSELECTIVE TOTAL SYNTHESIS OF 1-ALPHA,25S,26-TRIHYDROXYCHOLECALCIFEROL
WOVKULICH, PM
BARCELOS, F
BATCHO, AD
SERENO, JF
BAGGIOLINI, EG
HENNESSY, BM
USKOKOVIC, MR
[J]. TETRAHEDRON, 1984, 40 (12) : 2283 - 2296
[76] THERMAL AND TRIMETHYLSILYL TRIFLATE CATALYZED ADDITIONS OF ALLYLSILANES TO NITRONES
WUTS, PGM
JUNG, YW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) : 1957 - 1965
[77] AN EFFICIENT REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (+/-)-MONOMORINE-I VIA THE HIGHLY REGIOSELECTIVE ALPHA-ALKYNYLATION OF A 1-ACYLPYRIDINIUM SALT
YAMAGUCHI, R
HATA, E
MATSUKI, T
KAWANISI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) : 2094 - 2096
[78] ASYMMETRIC-SYNTHESIS WITH ALPHA,BETA-BIS[(METHOXYMETHYL)OXY] KETONES - ENANTIOSELECTIVE TOTAL SYNTHESIS OF NATURAL (+)-INDOLIZIDINE-195B (BICYCLIC GEPHYROTOXIN-195B) AND (-)-PINIDINE AND THEIR ENANTIOMERS FROM A COMMON CHIRAL SYNTHON
YAMAZAKI, N
KIBAYASHI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) : 1396 - 1408
[79] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-MONOMORINE-I
YAMAZAKI, N
KIBAYASHI, C
[J]. TETRAHEDRON LETTERS, 1988, 29 (45) : 5767 - 5768

← 1 2 3 4 5 6 7 8 →