Journal
ORGANIC LETTERS
Volume 18, Issue 18, Pages 4682-4685Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02322
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Funding
- National Science Foundation of China [21125207, 21372103, 21472079, 21572088]
- SRFDP [20130211110018]
- [IRT_15R28]
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The first asymmetric total synthesis of the structurally unique Lycopodium alkaloid (-)-lycospidine A, containing an unprecedented five-membered ring, has been accomplished in only 10 steps with 21.6% overall yield from the known conveniently available sulfoxide. This protecting-group-free short synthesis relied on the use of a key amidation/aza-Prins domino cyclization reaction to rapidly construct the tricyclic skeleton and two continuous stereocenters (one of which is a bridged quaternary stereocenter). An intramolecular aldol condensation was successfully utilized to establish the unique five-membered ring, and a late-stage oxidation inspired by biosynthesis pathway was adopted to synthesize the diosphenol ring of (-)-lycospidine A.
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