Formal total synthesis of aspergillide A

Autor:	Yuko Izuchi, Nobuhiro Kanomata, Yayoi Hongo, Tadashi Nakata, Hiroyuki Koshino, Shunya Takahashi
Rok vydání:	2011
Předmět:	Chemistry Stereochemistry Organic Chemistry Total synthesis Formyl group Catalysis Inorganic Chemistry chemistry.chemical_compound Hydrolysis Yield (chemistry) Physical and Theoretical Chemistry Allyl alcohol Enone Derivative (chemistry)
Zdroj:	Tetrahedron: Asymmetry. 22:246-251
ISSN:	0957-4166
Popis:	The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4–C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa’s key intermediate 2 for the total synthesis of 1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9c49c080e775b5865d09fd8a252079f8 https://doi.org/10.1016/j.tetasy.2011.01.016 Zobrazit plný text záznamu Full Text from ScienceDirect