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Diastereo‐ and enantioselective synthesis of the 18‐membered lichen macrolide (+)‐aspicilin
Author(s) -
Enders Dieter,
Prokopenko Oleg F.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199507161
Subject(s) - enantioselective synthesis , chemistry , hydrazone , stereocenter , alkylation , stereochemistry , stereoselectivity , organic chemistry , catalysis
The asymmetric synthesis of the lichen macrolide (+)‐aspicilin ( 1 ) was realised in 19 steps and with high stereoselectivity (de ≥ 91 %, ee ≥ 96%). Three of the four stereogenic centres were generated by employing the SAMP/RAMP hydrazone method. Key steps of the synthesis are the α,α′‐double alkylation of RAMP hydrazone ( R )‐ 10 of 2,2‐dimethyl‐1,3‐dioxan‐5‐one B and the enantioselective synthesis of the bromo alcohol ( S )‐ 9 (subunit A ) by a combination of SAMP hydrazone α‐alkylation with subsequent Baeyer‐Villiger oxidation.