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.
|Number of pages||11|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - 2014 Oct 1|
- Dötz benzannulation
- Fischer chromium carbene complex
ASJC Scopus subject areas
- Organic Chemistry