Total syntheses of ent-conduramine A and ent-7-deoxypancratistatin.

被引：51

作者：

Akgün, H ^{[1
]}

Hudlicky, T ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 16期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(99)00434-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the title alkaloid has been accomplished in fourteen steps form 1-bromo-4-iodobenzene or 1-fluoro-4-iodobenzene via chemoenzymatic production of the antipodal cis-diene diols 4. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3081 / 3084

页数：4

共 35 条

[1] NARCICLASINE-4-O-BETA-D-GLUCOPYRANOSIDE, A GLUCOSYLOXY AMIDIC PHENANTHRIDONE DERIVATIVE FROM PANCRATIUM-MARITIMUM
ABOUDONIA, AH
DEGIULIO, A
EVIDENTE, A
GABER, M
HABIB, AA
LANZETTA, R
ELDIN, AAS
[J]. PHYTOCHEMISTRY, 1991, 30 (10) : 3445 - 3448
[2] ENANTIOSELECTIVE BACTERIAL BIOTRANSFORMATION ROUTES TO CIS-DIOL METABOLITES OF MONOSUBSTITUTED BENZENES, NAPHTHALENE AND BENZOCYCLOALKENES OF EITHER ABSOLUTE-CONFIGURATION
ALLEN, CCR
BOYD, DR
DALTON, H
SHARMA, ND
BRANNIGAN, I
KERLEY, NA
SHELDRAKE, GN
TAYLOR, SC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) : 117 - 118
[3] Trifluoromethanesulfonic anhydride-4-(N,N-dimethylamino)pyridine as a reagent combination for effecting Bischler-Napieralski cyclisation under mild conditions: Application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine
Banwell, MG
Bissett, BD
Busato, S
Cowden, CJ
Hockless, DCR
Holman, JW
Read, RW
Wu, AW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) : 2551 - 2553
[4] Boyd DR, 1998, NAT PROD REP, V15, P309
[5] ENANTIOSPECIFIC SYNTHESIS OF (4S,5S,6S)-4,5,6-TRIHYDROXYCYCLOHEX-2-ENONE AND (+)-CONDURITOL-C FROM FLUOROBENZENE VIA MICROBIAL OXIDATION
CARLESS, HAJ
OAK, OZ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) : 61 - 62
[6] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS
CERIOTTI, G
[J]. NATURE, 1967, 213 (5076) : 595 - &
[7] Total synthesis of (+)-7-deoxypancratistatin and (+)-7-deoxy-trans-dihydronarciclasine
Chida, N
Jitsuoka, M
Yamamoto, Y
Ohtsuka, M
Ogawa, S
[J]. HETEROCYCLES, 1996, 43 (07) : 1385 - 1390
[8] TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN
DANISHEFSKY, S
LEE, JY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) : 4829 - 4837
[9] A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution
Doyle, TJ
Hendrix, M
VanDerveer, D
Javanmard, S
Haseltine, J
[J]. TETRAHEDRON, 1997, 53 (32) : 11153 - 11170
[10] FORMATION OF (+)-CIS-2,3-DIHYDROXY-1-METHYLCYCLOHEXA-4,6-DIENE FROM TOLUENE BY PSEUDOMONAS-PUTIDA
GIBSON, DT
HENSLEY, M
YOSHIOKA, H
MABRY, TJ
[J]. BIOCHEMISTRY, 1970, 9 (07) : 1626 - &

← 1 2 3 4 →