Journal
ORGANIC LETTERS
Volume 10, Issue 19, Pages 4363-4365Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801794f
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Funding
- NIGMS NIH HHS [R01 GM029028, R01 GM029028-25, R01 GM029028-26, R01 GM029028-24A1, GM-29028] Funding Source: Medline
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The total synthesis and assignment of absolute configuration of (-)-aplaminal (1), a cytotoxic metabolite from a sea hare possessing a triazobicyclo[3.2.1]octane skeleton, has been achieved. The synthesis entailed condensation of a monoprotected diamine (3) with dimethyl 2-oxomalonate (4) to generate the imidazolidine core (2). Introduction of the third nitrogen via Mitsunobu activation and azide displacement, followed by reduction and lactam formation (AIMe(3)), furnished (-)-aplaminal (1). Overall, the synthesis entailed 9 steps and proceeded in 19% overall yield.
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