Synthesis of Oxy-Functionalized Steroidal Skeletons
via Mizoroki–Heck and
Intramolecular Diels–Alder Reactions
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Posted on 2019-09-09 - 16:41
Estrogenic and cardiotonic
steroidal skeletons were concisely constructed via Mizoroki–Heck
and intramolecular Diels–Alder (IMDA) reactions. Simple modification
of the dienophile unsaturation of the IMDA precursor enabled representative
AB-ring systems of both steroid classes to be accessed from the same
intermediate. The diastereoselectivity of the IMDA reaction used to
access the cardiotonic steroidal skeleton was found to be significantly
enhanced by performing the reaction in water.
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Watanabe, Shogo; Nishikawa, Toshio; Nakazaki, Atsuo (2019). Synthesis of Oxy-Functionalized Steroidal Skeletons
via Mizoroki–Heck and
Intramolecular Diels–Alder Reactions. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02716