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Synthesis 2002(15): 2280-2288
DOI: 10.1055/s-2002-34949
DOI: 10.1055/s-2002-34949
PAPER
© Georg Thieme Verlag Stuttgart · New York
First Highly Efficient Asymmetric Synthesis of the Hyrtios Erectus Diketotriterpenoid
Weitere Informationen
Received
22 June 2002
Publikationsdatum:
21. Oktober 2002 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2002 (online)
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Abstract
The first highly efficient asymmetric synthesis of the diketotriterpenoid 1, isolated from the Indonesian marine sponge Hyrtios erectus, in good overall yield and employing simple starting materials such as butanone, is described. Both stereogenic centres at the C-6 and C-19 positions of the C 2-symmetrical molecule were generated via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric inductions (de, ee ≥ 96%). The absolute configuration of the natural material was determined as R,R.
Key words
asymmetric synthesis - hydrazones - alkylations - natural products - terpenoids
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