TY - JOUR
T1 - Construction of ansa-skeleton via intramolecular dötz benzannulation
T2 - Total synthesis of kendomycin
AU - Saikawa, Yoko
AU - Tanaka, Kyosuke
AU - Nakata, Masaya
PY - 2014/10/1
Y1 - 2014/10/1
N2 - 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.
AB - 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.
KW - Ansa-compound
KW - Dötz benzannulation
KW - Fischer chromium carbene complex
KW - Kendomycin
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U2 - 10.5059/yukigoseikyokaishi.72.1143
DO - 10.5059/yukigoseikyokaishi.72.1143
M3 - Article
AN - SCOPUS:84928783741
SN - 0037-9980
VL - 72
SP - 1143
EP - 1153
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
IS - 10
ER -