Synthetic Studies Towards Phorboxazole B: Stereoselective Synthesis of the C3-C19 Bis-oxane Oxazole Fragment

Dong-hui Zhang; Wei-shan Zhou

doi:10.1055/s-2003-41462

LETTER

Synthetic Studies Towards Phorboxazole B: Stereoselective Synthesis of the C3-C19 Bis-oxane Oxazole Fragment

Dong-hui Zhang, Wei-shan Zhou*
Shanghai Institute of Organic Chemistry, 354 Fenglin Rd, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: zhws@mail.sioc.ac.cn.;

Abstract

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Abstract

A convergent and enantioselective synthesis of the C3-C19 bis-oxane oxazole fragment of phorboxazole B has been described. This work features highly efficient substrate-controlled reductions to construct the functionalised cis-oxane and a Mukaiyama aldol reaction followed by an intramolecular Williamson reaction leading to a trans-oxane.

Key words

enantioselective synthesis - phorboxazole - reduction - Mukaiyama reaction - Williamson reaction

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References

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