Synthetic Studies on Siphonariid Polypropionates: Synthesis and Isomerization of the Caloundrin B Trioxaadamantane Ring System

被引：14

作者：

Beye, Garrison E. ^{[1
]}

Goodman, Jonathan M. ^{[2
]}

Ward, Dale E. ^{[1
]}

机构：

[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada

[2] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

THIOPYRAN ROUTE; ABSOLUTE-CONFIGURATION; MUAMVATIN; MODEL; BACONIPYRONES; METABOLITES; EFFICIENT; FRAGMENTS; ACETALS;

D O I：

10.1021/ol900192q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(1R,3R,5R,7R,8S,9R,10S)-3,5-Diethyl-8,9,10-trimethyl-2,4,6-trioxatricyclo[3.3.1.1(3,7)]decan-1-ol (II), a model of the trioxaadamantane ring system embedded in caloundrin B, was prepared by isomerization of the thermodynamically unstable (9S)-diastereomer (1) in the presence of imidazole. Alternatively, isomerization of I with HF.py or DBU gave the hemiacetal III or its retro-Claisen ester IV, respectively, which represent structural motifs present in the closely related siphonariid polypropionates siphonarin B and baconipyrone C.

引用

页码：1373 / 1376

页数：4

共 50 条

[1] On the Origin of Siphonariid Polypropionates: Total Synthesis of Caloundrin B and Its Isomerization to Siphonarin B
Becerril-Jimenez, Fabiola
Ward, Dale E.
ORGANIC LETTERS, 2012, 14 (06) : 1648 - 1651
[2] CALOUNDRIN-B AND FUNICULATIN-A - NEW POLYPROPIONATES FROM SIPHONARIID LIMPETS
BLANCHFIELD, JT
BRECKNELL, DJ
BRERETON, IM
GARSON, MJ
JONES, DD
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (12) : 2255 - 2269
[3] On the Origin of Siphonariid Polypropionates: Total Synthesis of Baconipyrone A, Baconipyrone C, and Siphonarin B via their Putative Common Precursor
Beye, Garrison E.
Ward, Dale E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 7210 - 7215
[4] Synthetic studies on ciguatoxin - [2]; Synthesis of the A,B,C-ring system
Oka, T
Fujiwara, K
Murai, A
TETRAHEDRON, 1998, 54 (1-2) : 21 - 44
[5] SYNTHETIC STUDIES ON CYATHINS - SYNTHESIS OF THE RING-SYSTEM
WARD, DE
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (10): : 2380 - 2384
[6] Synthetic studies on ciguatoxin. Part 2: Synthesis of the A,B,C-ring system
Oka, T.
Fujiwara, K.
Murai, A.
Tetrahedron, 54 (1-2):
[7] Synthetic studies on asperparaline A. Synthesis of the spirosuccinimide ring system
Gonzalez, F
Sanz-Cervera, JF
Williams, RM
TETRAHEDRON LETTERS, 1999, 40 (24) : 4519 - 4522
[8] SYNTHETIC STUDIES TOWARD CONCAVINE: SYNTHESIS OF THE BCD RING SYSTEM
Komori, Yosuke
Kozen, Akitoshi
Toyota, Masahiro
HETEROCYCLES, 2016, 93 (02) : 792 - 801
[9] Synthetic studies on brevetoxin-B. Part 1: Stereoselective synthesis of the ABC-ring system
Matsuo, G
Matsukura, H
Hori, N
Nakata, T
TETRAHEDRON LETTERS, 2000, 41 (40) : 7673 - 7676
[10] Synthetic studies on brevetoxin-B. Part 2. Stereoselective synthesis of the EFG-ring system
Matsuo, G
Hori, N
Matsukura, H
Nakata, T
TETRAHEDRON LETTERS, 2000, 41 (40) : 7677 - 7680

← 1 2 3 4 5 →