3 years ago

Synthesis of Allahabadolactone A

Synthesis of Allahabadolactone A
Roderick W. Bates, Kongchen Wang
A synthesis of allahabadolactone A is described employing diastereoselective Diels–Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels–Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels–Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02368

DOI: 10.1021/acs.joc.7b02368

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