Bicyclo[3.3.1] Nonanes as Synthetic Intermediates. Viii.¹ 1-Alkoxybicyclo [4.3.1] Decan-3-Onecarboxylates via the Anti-Bredt [4.3.1] System: An Improved Synthetic Route to Bicyclo [4.3.1] Decan-8-One

T. Momose Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka, 565, Japan

K. Masuda Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka, 565, Japan

O. Muraoka Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka, 565, Japan

Abstract

Bicyclo [4.3.1] decan-8-onecarboxylates bearing a bridgehead alkoxyl were prepared by facile interconversion of the alkoxyls, possibly via an anti-Bredt intermediate, and efficient removal of the ring substituents in the benzyloxy analog furnished a convenient synthesis of bicyclo [4.3.1] dec-an-8-one in 33% overall yield from cycloheptenone.

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Bicyclo[3.3.1] Nonanes as Synthetic Intermediates. Viii.¹ 1-Alkoxybicyclo [4.3.1] Decan-3-Onecarboxylates via the Anti-Bredt [4.3.1] System: An Improved Synthetic Route to Bicyclo [4.3.1] Decan-8-One

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Bicyclo[3.3.1] Nonanes as Synthetic Intermediates. Viii.1 1-Alkoxybicyclo [4.3.1] Decan-3-Onecarboxylates via the Anti-Bredt [4.3.1] System: An Improved Synthetic Route to Bicyclo [4.3.1] Decan-8-One

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Bicyclo[3.3.1] Nonanes as Synthetic Intermediates. Viii.¹ 1-Alkoxybicyclo [4.3.1] Decan-3-Onecarboxylates via the Anti-Bredt [4.3.1] System: An Improved Synthetic Route to Bicyclo [4.3.1] Decan-8-One