SYNTHESIS OF 1-DEOXYCASTANOSPERMINE AND STEREOISOMERS

被引：51

作者：

STDENIS, Y ^{[1
]}

CHAN, TH ^{[1
]}

机构：

[1] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2K6,QUEBEC,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 11期

关键词：

D O I：

10.1021/jo00037a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.

引用

页码：3078 / 3085

页数：8

共 28 条

[1] ENANTIOSELECTIVE SYNTHESIS OF SWAINSONINE, A TRIHYDROXYLATED INDOLIZIDINE ALKALOID
ADAMS, CE
WALKER, FJ
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) : 420 - 422
[2] TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE
APPEL, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12): : 801 - 811
[3] SYNTHESIS OF THE ALPHA-MANNOSIDASE INHIBITORS SWAINSONINE [(1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE] AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE
BASHYAL, BP
FLEET, GWJ
GOUGH, MJ
SMITH, PW
[J]. TETRAHEDRON, 1987, 43 (13) : 3083 - 3093
[4] A SHORT, ENANTIOSELECTIVE SYNTHESIS OF (-)-SWAINSONINE
BENNETT, RB
CHOI, JR
MONTGOMERY, WD
CHA, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2580 - 2582
[5] A CHEMOENZYMATIC SYNTHESIS OF (+)-CASTANOSPERMINE
BHIDE, R
MORTEZAEI, R
SCILIMATI, A
SIH, CJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4827 - 4830
[6] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE
CHA, JK
CHRIST, WJ
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 3943 - 3946
[7] CHA JK, 1983, TETRAHEDRON LETT, V24, P3947
[8] CHEREST M, 1968, TETRAHEDRON LETT, P2199
[9] STUDIES IN STEREOCHEMISTRY .20. STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE PREPARATION OF THE 3-CYCLOHEXYL-2-BUTANOL SYSTEM
CRAM, DJ
GREENE, FD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (23) : 6005 - 6010
[10] STUDIES IN STEROECHEMISTRY .32. MODELS FOR 1,2-ASYMMETRIC INDUCTION
CRAM, DJ
WILSON, DR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (09) : 1245 - &

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