A biogenetically patterned synthetic approach to the unusual furan methylenecyclobutanol moiety in providencin

被引：29

作者：

Bray, Christopher D. ^{[1
]}

Pattenden, Gerald ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 23期

关键词：

D O I：

10.1016/j.tetlet.2006.03.158

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of a solution of alpha,beta-unsaturated aldehyde 10 in benzene leads to the methylenecyclobutanol 11 by way of a novel intrarnolecular C-H insertion reaction. The conversion of 10 into 11 has relevance to the possible origin of the cyclobutane ring-based furanocembrane providencin 1 found in gorgonian octocorals. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3937 / 3939

页数：3

共 19 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2] Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin [J].

Cases, M ;

de Turiso, FGL ;

Hadjisoteriou, MS ;

Pattenden, G .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (15) :2786-2804

[3]

Cases M, 2001, SYNLETT, P1869

[4] Progress toward the total synthesis of bielschowskysin: A stereoselective [2+2] photocycloaddition [J].

Doroh, B ;

Sulikowski, GA .

ORGANIC LETTERS, 2006, 8 (05) :903-906

[5]

Epifanio RD, 2000, J BRAZIL CHEM SOC, V11, P584

[6] MARINE SOFT CORALS OF THE GENUS PSEUDOPTEROGORGIA - A RESOURCE FOR NOVEL ANTI-INFLAMMATORY DITERPENOIDS [J].

FENICAL, W .

JOURNAL OF NATURAL PRODUCTS, 1987, 50 (06) :1001-1008

[7]

Hansen T. V., 2001, ORGANIC SYNTHESIS TH, V5, P1

[8] Marine natural products from Pseudopterogorgia elisabethae:: Structures, biosynthesis, pharmacology, and total synthesis [J].

Heckrodt, TJ ;

Mulzer, J .

NATURAL PRODUCTS SYNTHESIS II TARGETS, METHODS, CONCEPTS, 2005, 244 :1-41

[9] Total synthesis of (±)-bipinnatin J [J].

Huang, QH ;

Rawal, VH .

ORGANIC LETTERS, 2006, 8 (03) :543-545

[10]

KATZ E, 2000, STUD NAT PROD CHEM, V23, P153

← 1 2 →