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. Author manuscript; available in PMC: 2020 Dec 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2020 Aug 24;59(43):18898–18919. doi: 10.1002/anie.201915657

Scheme 8.

Scheme 8.

A) Retrosynthesis and B) total synthesis of (−)-cycloclavine. Boc = tert-butoxycarbonyl, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, DOSP = N-(dodecylbenzenesulfonyl)prolinate, (R)-DTBM-segphos = (R)-(−)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]4,4’-bi-1,3-ben-zodioxole, OTf = triflate, TFA = trifluoroacetic acid, Ts = tosyl.