| Abstract
| - A highly convergent total synthesis of bitungolide F leadingto the assignment of its absolute stereochemistry is described.The key steps include a Horner−Wadsworth−Emmonsolefination to construct the C7−C8 bond, a Wittig reactionto introduce the conjugate E,E-olefinic moiety in themolecule, and finally a ring-closing metathesis reaction toconstruct the six-membered α,β-unsaturated δ-lactone of themolecule. Modified Evans's syn-aldol reaction, using Crimmins's protocol, was used to install the stereochemistries atthe C4 and C5 centers. The stereochemistry at C9 wasintroduced by means of hydroxy-directed reduction of theC9 keto using Evans's protocol.
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