Total Synthesis of Swinhoeisterol A, Dankasterones A and B, and Periconiastone A

Key words

swinhoeisterol A - dankasterone A - dankasterone B - periconiastone A - radical rearrangement - skeleton rearrangement

Significance

Heretsch and co-workers report the total synthesis of a number of structurally intriguing natural products from a common intermediate. The concise synthesis is enabled by the strategic application of a switchable alkoxy radical rearrangement.

Comment

Ergosterol is transformed by a known route to cyclopropane A. Two different conditions were developed to lead selectively to B or C. Those advanced intermediates could subsequently be converted into four different complex natural products.