Total synthesis of (-)-anisatin

Akihiro Ogura, Kohei Yamada, Satoshi Yokoshima, Tohru Fukuyama

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

A novel synthetic route to (-)-anisatin has been developed. Our synthesis features a rhodium-catalyzed 1,4-addition of an arylboronic acid, an intramolecular Diels-Alder reaction of an ortho-quinone monoketal, a stereoselective [2,3]-Wittig rearrangement, and construction of the oxabicyclo [3.3.1] skeleton via cleavage of an epoxide by a primary amide.

Original languageEnglish
Pages (from-to)1632-1635
Number of pages4
JournalOrganic Letters
Volume14
Issue number6
DOIs
Publication statusPublished - 2012 Mar 16
Externally publishedYes

Fingerprint

Diels-Alder reactions
Rhodium
epoxy compounds
Epoxy Compounds
Cycloaddition Reaction
quinones
rhodium
musculoskeletal system
Skeleton
Amides
amides
cleavage
routes
acids
Acids
synthesis
benzoquinone
anisatin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ogura, A., Yamada, K., Yokoshima, S., & Fukuyama, T. (2012). Total synthesis of (-)-anisatin. Organic Letters, 14(6), 1632-1635. https://doi.org/10.1021/ol300390k

Total synthesis of (-)-anisatin. / Ogura, Akihiro; Yamada, Kohei; Yokoshima, Satoshi; Fukuyama, Tohru.

In: Organic Letters, Vol. 14, No. 6, 16.03.2012, p. 1632-1635.

Research output: Contribution to journalArticle

Ogura, A, Yamada, K, Yokoshima, S & Fukuyama, T 2012, 'Total synthesis of (-)-anisatin', Organic Letters, vol. 14, no. 6, pp. 1632-1635. https://doi.org/10.1021/ol300390k
Ogura A, Yamada K, Yokoshima S, Fukuyama T. Total synthesis of (-)-anisatin. Organic Letters. 2012 Mar 16;14(6):1632-1635. https://doi.org/10.1021/ol300390k
Ogura, Akihiro ; Yamada, Kohei ; Yokoshima, Satoshi ; Fukuyama, Tohru. / Total synthesis of (-)-anisatin. In: Organic Letters. 2012 ; Vol. 14, No. 6. pp. 1632-1635.
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