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Asymmetric Synthesis of (+)‐ and (–)‐Streptenol A
Author(s) -
Enders Dieter,
Hundertmark Thomas
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199904)1999:4<751::aid-ejoc751>3.0.co;2-r
Subject(s) - chemistry , deoxygenation , hydrazone , aldehyde , alkylation , yield (engineering) , enantiomer , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
The asymmetric synthesis of (+)‐streptenol A was carried out in ten steps and with high enantioselectivity (ee ≥ 96%). The key steps are the α‐alkylation of 2,2‐dimethyl‐1,3‐dioxan‐5‐one RAMP hydrazone A (1), subsequent deoxygenation and elaboration of the side chain via aldehyde B to furnish (+)‐streptenol A in 23% overall yield. In analogy, the enantiomer (–)‐streptenol A was synthesized using the corresponding SAMP hydrazone in 18% overall yield.