ISSN:
0947-3440
Keywords:
(+)-Aspicilin
;
Macrolide, asymmetric synthesis of
;
SAMP/RAMP hydrazones, diastereoselective alkylation
;
2,2-Dimethyl-1,3-dioxan-5-one
;
Baeyer-Villiger reaction
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199507161
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