76023-93-3Relevant articles and documents
Asymmetric synthesis of quaternary centers. Total synthesis of (-)-malyngolide.
Trost,Tang,Schulte
, p. 4013 - 4015 (2000)
[structure] The deracemization of 3-nonyl-3,4-epoxybut-1-ene with Pd(0) in the presence of chiral ligands using p-methoxybenzyl alcohol as a nucleophile proceeds regio- and enantioselectively to form the monoprotected vinylglycidol in 99% ee. This chiral building block was converted in seven steps to (-)-malyngolide, an antibiotic showing significant activity against Mycobacterium smegmatis and Streptococcus pyogenes. An interesting aspect involves controlling the diastereoselectivity of protonation of an enolate via a distal hydroxyl group.
Enantioselective total synthesis of δ-lactonic marine natural products, (+)-tanikolide and (-)-malyngolide, via RCM reaction
Mizutani, Hirotake,Watanabe, Masayuki,Honda, Toshio
, p. 8929 - 8936 (2007/10/03)
Enantioselective total synthesis of δ-lactonic marine natural products, (+)-tanikolide and (-)-malyngolide isolated from Lyngbya majuscula, was achieved by using the Sharpless asymmetric epoxidation and a ring-closing metathesis, as key reactions.
Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: Application to the synthesis of (-)-malyngolide
Date,Tamai,Hattori,Takayama,Kamikubo,Miyano
, p. 645 - 653 (2007/10/03)
Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of podand-type δ- (3,4) and ε-keto esters (5,6) are achieved in the presence of MgBr2·OEt2 with up to 97 and 82% optical yields, respectively, by using 2′-[3-(2-methoxyethoxy)propoxy]-1,1′-binaphthalen-2-ol as the chiral auxiliary. The 1,8-asymmetric inductive Grignard reaction has been advantageously utilized in the key step of a synthesis of (-)-malyngolide.
