Total synthesis and stereochemical assignment of myriaporones 1, 3, and 4

被引：41

作者：

Fleming, KN ^{[1
]}

Taylor, RE ^{[1
]}

机构：

[1] Univ Notre Dame, Walther Canc Res Ctr, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 13期

关键词：

aldol reaction; diastereoselectivity; epoxidation; natural products; total synthesis;

D O I：

10.1002/anie.200353348

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two stereoselective aldol reactions, a nitrile oxide cycloaddition, and a stereoselective late-stage epoxidation were key steps in the total synthesis of myriaporones 1, 3, and 4 (see scheme). The synthesis allowed the unambiguous assignment of stereogenic centers not previously assigned for these compounds.

引用

页码：1728 / 1730

页数：3

共 24 条

[1]

BARALDI PG, 1987, SYNTHESIS-STUTTGART, P276

[2] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[3] ALDOL ADDITION-REACTIONS OF CHIRAL CROTONATE IMIDES [J].

EVANS, DA ;

SJOGREN, EB ;

BARTROLI, J ;

DOW, RL .

TETRAHEDRON LETTERS, 1986, 27 (41) :4957-4960

[4] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].

FRIGERIO, M ;

SANTAGOSTINO, M .

TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022

[5] BIOACTIVE MARINE METABOLITES .35. CYTOTOXIC METABOLITES OF THE MARINE SPONGE MYCALE-ADHAERENS LAMBE [J].

FUSETANI, N ;

SUGAWARA, T ;

MATSUNAGA, S ;

HIROTA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4971-4974

[6] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[7]

Hassfeld J, 2002, SYNLETT, P2007

[8] Efficient synthesis of the C1-C11 fragment of the tedanolides.: The nonaldol aldol process in synthesis [J].

Jung, ME ;

Marquez, R .

ORGANIC LETTERS, 2000, 2 (12) :1669-1672

[9] Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters [J].

Liu, JF ;

Abiko, A ;

Pei, ZH ;

Buske, DC ;

Masamune, S .

TETRAHEDRON LETTERS, 1998, 39 (14) :1873-1876

[10] Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment [J].

Loh, TP ;

Feng, LC .

TETRAHEDRON LETTERS, 2001, 42 (18) :3223-3226

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