Abstract
Enantiomerically pure (+)-(5 S)-dihydroyashabushiketol 1a was obtained by the 1,3-dipolar cycloaddition of a nitrile oxide, generated from oxime 3b, to N-acryloyl bornane[10,2]sultam (2 R)- 2 (67%, 85% de, then crystallization 81%, 99% de), followed by reduction with DIBAL-H to aldehyde (−)- 6a (67%), Wittig reaction to isoxazoline ( E/ Z)- 7 (60%), and finally hydrolytic hydrogenation (62%).
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