A formal total synthesis of (+)-methyl trachyloban-18-oate and (+)-methyl 16-oxo-17-norkauran-18-oate: Regio- and diastereoselective preparation of methyl (13S)-13-hydroxyisoatisiren-18-oate from (-)-abietic acid

被引：17

作者：

Berettoni, M ^{[1
]}

DeChiara, G ^{[1
]}

Iacoangeli, T ^{[1
]}

LoSurdo, P ^{[1
]}

Bettolo, RM ^{[1
]}

diMirabello, LM ^{[1
]}

Nicolini, L ^{[1
]}

Scarpelli, R ^{[1
]}

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,I-00185 ROME,ITALY

来源：

HELVETICA CHIMICA ACTA | 1996年 / 79卷 / 07期

关键词：

D O I：

10.1002/hlca.19960790724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel preparation of methyl (13S)-13-hydroxyisoatisiren-18-oate (4), a key-intermediate in a synthesis of (+)-methyl trachyloban-18-oate ((+)-1), from (-)-abietic acid, is described. Since (-)-1 has been previously convened into (-)-methyl 16-oxo-17-norkauran-18-oate ((-)-16), our preparation of 4 constitutes also a formal total synthesis, from (-)-abietic acid, of (+)-16. Key steps in this approach were the allene photoaddition to podocarp-8(14)-en-13-one (5) and the conversion of the endo-toluene-4-sulfonate 11 into the exo-benzoate 12b.

引用

页码：2035 / 2041

页数：7

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