Fusicoccin ring system by [4+4] cycloaddition. 2. A model study

被引：11

作者：

Sieburth, SM ^{[1
]}

McGee, KF ^{[1
]}

Al-Tel, TH ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期

基金：

美国国家卫生研究院;

关键词：

cycloaddition; natural products; photochemistry; pyridones;

D O I：

10.1016/S0040-4039(99)00671-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to fusicoccin A utilizing intramolecular photocycloaddition of tethered 2-pyridones has been completed. This study has led to the first solvent-dependent 2-pyridone photocycloaddition yielding either cis or trans products. Epoxidation of the cis photoproduct is selective for the disubstituted alkene, stabilizes the product, and is properly located for installation of the trans-1,2-diol. Activation of the secondary amide by reaction with an isocyanate led to the reduction of the neopentyl amide carbonyl to a methyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4007 / 4010

页数：4

共 34 条

[1] NEW SYNTHETIC APPROACHES TO FUSED-RING CARBOCYCLES BASED ON INTRAMOLECULAR PHOTOCYCLOADDITIONS OF 1,3-DIONE ENOL ESTERS
BEGLEY, MJ
MELLOR, M
PATTENDEN, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08): : 1905 - 1912
[2] SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .1. TOTAL SYNTHESIS OF (+/-)-CEROPLASTOL-I
BOECKMAN, RK
ARVANITIS, A
VOSS, ME
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2737 - 2739
[3] SYNTHESIS OF STEREOISOMERIC 4,9A-DIMETHYLHYDRODICYCLOPENTA[A,D]CYCLOOCTEN-1-ONES RELATED TO THE OPHIOBOLINS AND CEROPLASTINS VIA ANNELATIVE RING EXPANSION OF HYDRINDENE PRECURSORS
COATES, RM
MUSKOPF, JW
SENTER, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) : 3541 - 3557
[4] DIOXIRANE OXIDATIONS - TAMING THE REACTIVITY-SELECTIVITY PRINCIPLE
CURCI, R
DINOI, A
RUBINO, MF
[J]. PURE AND APPLIED CHEMISTRY, 1995, 67 (05) : 811 - 822
[5] SYNTHESIS OF OPHIOBOLIN NUCLEUS
DAUBEN, WG
HART, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) : 922 - 923
[6] AN APPROACH TOWARD THE OPHIOBOLANE SESTERTERPENES - SYNTHESIS OF THE CEROPLASTIN NUCLEUS
DAUBEN, WG
WARSHAWSKY, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3075 - 3087
[7] A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS
FLYNN, DL
ZELLE, RE
GRIECO, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) : 2424 - 2426
[8] FUJIMOTO Y, 1976, TETRAHEDRON LETT, P3325
[9] SYNTHESIS OF THE FUSICOCCIN-H AGLYCONE - CONSTRUCTION OF THE CARBON FRAMEWORK
GRAYSON, DH
WILSON, JRH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (24) : 1695 - 1696
[10] Intramolecular cycloaddition reactions of allylic cations
Harmata, M
[J]. TETRAHEDRON, 1997, 53 (18) : 6235 - 6280

← 1 2 3 4 →