Journal
ORGANIC LETTERS
Volume 19, Issue 18, Pages 4892-4895Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02349
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Funding
- Swedish Chemical Society
- Swedish Pharmaceutical Society
- National Institute of General Medical Sciences [GM065483]
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A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.
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