Construction of ansa-skeleton via intramolecular dötz benzannulation: Total synthesis of kendomycin

Yoko Saikawa, Kyosuke Tanaka, Masaya Nakata

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Ansa-compounds have intriguing molecular structures and highly potent bioactivities. One of the ansa-compounds, kendomycin, has an oxa-metacyclophane skeleton with quinone methide core and a fully substituted tetrahydropyran ring. In contrast to a common synthetic strategy for construction of the ansa-skeleton via elongation of an alkyl chain from an aromatic core followed by macrocyclizalion, we challenged a new method for construction of the ansa-skeleton via simultaneous macrocyclizalion and benzannulation (using intramolecular Dötz benzannulation). Understanding the reactivity of various Fischer-type Ω-alkynyloxy chromium carbene complexes with kendomycin analogs syntheses led to achievement of the total synthesis of kendomycin. Investigations of structure-activity relationships revealed the need for an ansa-skeleton for antimicrobial activity.

Original languageEnglish
Pages (from-to)1143-1153
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume72
Issue number10
DOIs
Publication statusPublished - 2014 Oct 1

Keywords

  • Ansa-compound
  • Dötz benzannulation
  • Fischer chromium carbene complex
  • Kendomycin

ASJC Scopus subject areas

  • Organic Chemistry

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