Literature DB >> 34820990

Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A.

Benjamin J Huffman1, Tiffany Chu1, Yusuke Hanaki1, Jonathan J Wong2, Shuming Chen3, Kendall N Houk2, Ryan A Shenvi1.   

Abstract

A strategy to control the diastereoselectivity of bond formation at a prochiral attached-ring bridgehead is reported. An unusual stereodivergent Michael reaction relies on basic vs. Lewis acidic conditions and non-covalent interactions to control re- vs. si- facial selectivity en route to fully substituted attached-rings. This divergency reflects differential engagement of one rotational isomer of the attached-ring system. The successful synthesis of an erythro subtarget diastereomer ultimately leads to a short formal synthesis of merrilactone A.
© 2021 Wiley-VCH GmbH.

Entities:  

Keywords:  Michael addition; attached-ring; diastereoselectivity; natural products; synthesis design

Mesh：

Substances：

Year:  2021        PMID： 34820990      PMCID： PMC8748398          DOI： 10.1002/anie.202114514

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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