Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 18, Pages 9488-9493Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401412g
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Funding
- National Basic Research Program (973 Program) of China [2010CB833200]
- NSF of China [21072160, 20832005]
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We report herein for the first time the enantioselective synthesis of 8-aza-PGE(1). The synthesis used the cross olefin metathesis reaction to connect the 5-vinyl-gamma-lactam subunit, prepared from (R)-malic acid via the Ley's sulfone-based alpha-amidalkylation protocol (dr = 6.8:1), with the chiral pre-omega-chain. The latter was synthesized in high enantioselectivity from (E)-2-octenol by the Sharpless asymmetric epoxidation and the titanocene-mediated epoxide opening. This modular approach is quite concise and flexible, and requires only eight steps from commercially available reagents.
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