The stereoselective total synthesis of (-)-microcarpalide, a recently discovered 10-membered lactone of fungal origin displaying a remarkable disrupting action on actin micro. laments, was accomplished by using ring-closing metathesis (RCM) as the key step for the formation of the medium-sized ring. The diene ester required for the macrocyclization reaction was assembled via DCC-mediated esterification of two suitable partners, each bearing a terminal alkene group. The alcohol fragment was synthesized from n-bromohexane through a seven-step sequence entailing two consecutive stereoselective homologations of chiral boronic esters as strategic transformations for the sequential insertion of the two stereocentres with the final S absolute configuration, using (+)-pinanediol as the chiral director; final elaboration to the desired C-11 framework envisaged treatment with an allyl Grignard reagent and oxidative cleavage of the boronic scaffold. In contrast, the acidic fragment was prepared in ten steps from D-tartaric acid, whose C-4 backbone was elongated to the required C-7 skeleton by means of two distinct Swern-Wittig oxidation - homologation sequences.

Total synthesis of )-microcarpalide, a novel microfilament disrupting metabolite / Davoli, Paolo; Spaggiari, Alberto; L., Castagnetti; Prati, Fabio. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 2:1(2004), pp. 38-47. [10.1039/b308709c]

Total synthesis of )-microcarpalide, a novel microfilament disrupting metabolite

DAVOLI, Paolo;SPAGGIARI, Alberto;PRATI, Fabio
2004

Abstract

The stereoselective total synthesis of (-)-microcarpalide, a recently discovered 10-membered lactone of fungal origin displaying a remarkable disrupting action on actin micro. laments, was accomplished by using ring-closing metathesis (RCM) as the key step for the formation of the medium-sized ring. The diene ester required for the macrocyclization reaction was assembled via DCC-mediated esterification of two suitable partners, each bearing a terminal alkene group. The alcohol fragment was synthesized from n-bromohexane through a seven-step sequence entailing two consecutive stereoselective homologations of chiral boronic esters as strategic transformations for the sequential insertion of the two stereocentres with the final S absolute configuration, using (+)-pinanediol as the chiral director; final elaboration to the desired C-11 framework envisaged treatment with an allyl Grignard reagent and oxidative cleavage of the boronic scaffold. In contrast, the acidic fragment was prepared in ten steps from D-tartaric acid, whose C-4 backbone was elongated to the required C-7 skeleton by means of two distinct Swern-Wittig oxidation - homologation sequences.
2004
2
1
38
47
Total synthesis of )-microcarpalide, a novel microfilament disrupting metabolite / Davoli, Paolo; Spaggiari, Alberto; L., Castagnetti; Prati, Fabio. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 2:1(2004), pp. 38-47. [10.1039/b308709c]
Davoli, Paolo; Spaggiari, Alberto; L., Castagnetti; Prati, Fabio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/305286
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