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. Author manuscript; available in PMC: 2017 Sep 13.
Published in final edited form as: Nat Prod Rep. 2011 May 9;28(7):1229–1260. doi: 10.1039/c0np00013b

Scheme 13.

Scheme 13

a) Proposed aziridinium intermediate suggested by an observed retention of configuration displacement of chloride by azide. b) Romo’s proposed biosynthesis of massadine based on this observation (ref. 37)