Formal total synthesis of aspergillide A

Yuko Izuchi, Nobuhiro Kanomata, Hiroyuki Koshino, Yayoi Hongo, Tadashi Nakata, Shunya Takahashi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)246-251
Number of pages6
JournalTetrahedron Asymmetry
Issue number2
Publication statusPublished - 2011 Jan 31

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


Dive into the research topics of 'Formal total synthesis of aspergillide A'. Together they form a unique fingerprint.

Cite this