1. Synthetic studies directed toward the AB decalin common to HMP-Y1 and hibarimicinone.
- Author
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Hempel, Jonathan E., Engers, Darren W., and Sulikowski, Gary A.
- Subjects
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DECAHYDRONAPHTHALENE , *ORGANIC synthesis , *RING formation (Chemistry) , *INTERMOLECULAR interactions , *KETONES , *MICHAEL reaction - Abstract
Abstract: Efforts toward the synthesis of the decalin ring system common to the hibarimicin shunt metabolite HMP-Y1 and parent aglycone hibarimicinone are reported herein. An intramolecular Diels–Alder cyclization rapidly generated the decalin framework. Two approaches toward completion of the AB decalin were vetted. Incorporation of a phenylsulfonyl leaving group β- to both a ketone and a γ-lactone followed by base-induced elimination of sulfinate led to the undesired α,β-unsaturated lactone. Methanolysis of the γ-lactone followed by elimination produced the unexpected bridged cyclic ether by way of an intramolecular oxy-Michael addition of the endo oriented C13 alcohol. [Copyright &y& Elsevier]
- Published
- 2014
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