Organic Letters
Organic Letters
4 years ago

Double-Diels–Alder Approach to Maoecrystal V. Unexpected C–C Bond-Forming Fragmentations of the [2.2.2]-Bicyclic Core

Double-Diels–Alder Approach to Maoecrystal V. Unexpected C–C Bond-Forming Fragmentations of the [2.2.2]-Bicyclic Core
Jon T. Njardarson, Brandon R. Smith
Synthetic studies toward maoecrystal V are reported. An oxidative dearomatization/Diels–Alder cascade to assemble the natural product carbocyclic core in one step is proposed. A facile electrocyclization is shown to suppress the intramolecular allene Diels–Alder pathway. This obstacle is alleviated via a stepwise approach with an allene equivalent to access the key cyclopentadiene-fused [2.2.2]-bicyclic core. Upon treatment with Lewis acid, the proposed intramolecular hetero-Diels–Alder reaction is cleanly and unexpectedly diverted either via C–C bond-forming fragmentation to the spiro-indene product (when R = OMe) or via elimination (when R = H).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02606

DOI: 10.1021/acs.orglett.7b02606

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