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Diastereo- and enantioselective synthesis of the 18-membered lichen macrolide (+)-aspicilin

✍ Scribed by Enders, Dieter ;Prokopenko, Oleg F.

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
865 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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A Concise Total Synthesis of the Lichen
A Concise Total Synthesis of the Lichen Macrolide (+)-Aspicilin.
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