Total synthesis of (+)-4-deoxygigantecin

被引：25

作者：

Makabe, H

Tanaka, A

Oritani, T

机构：

[1] TOHOKU UNIV,FAC AGR,DEPT APPL BIOL CHEM,GRAD SCH AGR,AOBA KU,SENDAI,MIYAGI 981,JAPAN

[2] TOHOKU UNIV,FAC AGR,DIV ENVIRONM BIOREMEDIAT,GRAD SCH AGR,AOBA KU,SENDAI,MIYAGI 981,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(97)00856-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-4-Deoxygigantecin (1) was totally synthesized from enantiomerically pure (-)-muricatacin (3). Thus, 3 afforded the key intermediate 5 through a five-step reaction sequence, which was then converted to (+)-4-deoxygigantecin (1) via the formation of bis-tetrahydrofuran unit 1 1 and a coupling reaction with iodo lactone synthon 1 6. (C) 1997 Elsevier Science Ltd.

引用

页码：4247 / 4250

页数：4

共 23 条

[1] CAVE A, 1993, RECENT ADV PHYTOCHEM, V27, P167
[2] CHEMOSELECTIVITY OF RHODIUM CARBENOIDS - A COMPARISON OF THE SELECTIVITY FOR O-H INSERTION REACTIONS OR CARBONYL YLIDE FORMATION VERSUS ALIPHATIC AND AROMATIC C-H INSERTION AND CYCLOPROPANATION
COX, GG
MOODY, CJ
AUSTIN, DJ
PADWA, A
[J]. TETRAHEDRON, 1993, 49 (23) : 5109 - 5126
[3] ANNONACEOUS-ACETOGENINS - AN UPDATED REVIEW - APPENDIXES
FANG, XP
RIESER, MJ
GU, ZM
ZHAO, GX
MCLAUGHLIN, JL
[J]. PHYTOCHEMICAL ANALYSIS, 1993, 4 (02) : 49 - 67
[4] ANNONACEOUS ACETOGENINS - AN UPDATED REVIEW
FANG, XP
RIESER, MJ
GU, ZM
ZHAO, GX
MCLAUGHLIN, JL
[J]. PHYTOCHEMICAL ANALYSIS, 1993, 4 (01) : 27 - 48
[5] FANG XP, 1992, HETEROCYCLES, V34, P1075
[6] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES
FIGADERE, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) : 359 - 365
[7] GU ZM, 1995, RECENT ADV PHYTOCHEM, V29, P249
[8] SYNTHESIS OF (-)-BULLATACIN - THE ENANTIOMER OF A POTENT, ANTITUMOR, 4-HYDROXYLATED, ANNONACEOUS ACETOGENIN
HOYE, TR
HANSON, PR
[J]. TETRAHEDRON LETTERS, 1993, 34 (32) : 5043 - 5046
[9] SYNTHESIS OF (+)-(15,16,19,20,23,24)-HEXEPI-UVARICIN - A BIS(TETRAHYDROFURANYL) ANNONACEOUS ACETOGENIN ANALOG
HOYE, TR
HANSON, PR
KOVELESKY, AC
OCAIN, TD
ZHUANG, ZP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9369 - 9371
[10] Highly efficient synthesis of the potent antitumor annonaceous acetogenin (+)-parviflorin
Hoye, TR
Ye, ZX
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) : 1801 - 1802

← 1 2 3 →