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. Author manuscript; available in PMC: 2014 Jan 25.
Published in final edited form as: J Am Chem Soc. 2012 Jul 25;134(31):13108–13113. doi: 10.1021/ja305342f

Scheme 6.

Scheme 6

Transesterification/ Ester-Amide Exchange toward Ponapensin and Elliptifoline

a) From 9a: Me3Al (20 equiv), amine 18 (20 equiv) toluene (0.3 M) 70 °C for 12 h (64%); from 9b: i) H2-Pd/C then ii) EDCI (1.5 equiv), HOBt (1.2 equiv), amine 18 (2.5 equiv) (95%, 2 steps); b) Otera’s catalyst (20 mol%), BnOH, 110 °C, house vacuum, 24 h (64%, recovery 28% 9b).