Volume 18, Issue 35
Heterocyclic Compounds
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ChemInform Abstract: Nucleophilic Additions to Thionolactones. New Synthetic Technology for the Construction of Medium- and Large-Ring Ethers.

K. C. NICOLAOU

K. C. NICOLAOU

Dep. Chem., Univ. Pa., Philadelphia, PA 19104, USA

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D. G. MCGARRY

D. G. MCGARRY

Dep. Chem., Univ. Pa., Philadelphia, PA 19104, USA

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P. K. SOMERS

P. K. SOMERS

Dep. Chem., Univ. Pa., Philadelphia, PA 19104, USA

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C. A. VEALE

C. A. VEALE

Dep. Chem., Univ. Pa., Philadelphia, PA 19104, USA

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G. T. FURST

G. T. FURST

Dep. Chem., Univ. Pa., Philadelphia, PA 19104, USA

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First published: September 1, 1987

Abstract

Thionolactones such as (I) can be conveniently transformed to substituted cyclic ethers such as (V) via addition products such as (IV) which are subsequently desulfurized to (V).

ChemInform Abstract

Thionolactones such as (I) can be conveniently transformed to substituted cyclic ethers such as (V) via addition products such as (IV) which are subsequently desulfurized to (V). Similarly, the compounds (VI)-(IX) are prepared in high yields. The convenient and clean generation of the free radical species (XI) allows the construction of the complex polycyclic systems (XII) and (XIII). Furthermore,an application of the described technology provides a short and efficient total synthesis of (±)-lauthisan (XVI) from the precursor (XV).

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