Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6595-6599Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02358
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Funding
- National Institutes of Health-NIGMS [R01 GM080266, R35 GM134725]
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While semisynthesis is a common platform for medicinal investigation of steroidal systems, varying the nature of substitution and stereochemistry at C9 and C10 remains challenging. It is demonstrated here that de novo synthesis, enabled by a metallacycle-centered annulation reaction, provides a uniquely effective means of addressing this problem. In short, double asymmetric Friedel-Crafts cyclization proved most effective for establishing anti- relative stereochemistry (with respect to C13), while an intramolecular Heck reaction reliably delivered the syn- diastereomers with high selectivity. In addition, these studies reveal that this oxidative rearrangement is effective for establishing a C10 quaternary center boasting variable alkyl or aryl substitution.
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