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. Author manuscript; available in PMC: 2019 Sep 21.
Published in final edited form as: Org Lett. 2018 Sep 10;20(18):5922–5926. doi: 10.1021/acs.orglett.8b02599

Scheme 2. Proposed Mechanism for Stereoselectivity in Ulbactin Formationa.

Scheme 2.

aThe reaction is selective for ulbactin F over G due to a favored chairlike transition state. A similar model applies to epi-ulbactin F over epi-ulbactin G.