Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach DOI
Atsushi Nakayama,

Hidemitsu Yamanaka,

Rika Yamasaki

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

(+)-Aigialospirol and (+)-7',8'-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus Aigialus parvus BCC 5311. These polyketides structurally characterized by fusing resorcylic acid lactone moieties containing six asymmetric carbon centers. In this paper, we describe concise stereoselective syntheses of these based on biosynthesis-inspired transformation in nine steps. The total highlighted a one-pot stepwise synthesis involving (i) ring formation chiral epoxide, (ii) reduction alkyne, (iii) global deprotection, (iv) formation, which performed the final step synthesis.

Language: Английский

Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach DOI
Atsushi Nakayama,

Hidemitsu Yamanaka,

Rika Yamasaki

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

(+)-Aigialospirol and (+)-7',8'-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus Aigialus parvus BCC 5311. These polyketides structurally characterized by fusing resorcylic acid lactone moieties containing six asymmetric carbon centers. In this paper, we describe concise stereoselective syntheses of these based on biosynthesis-inspired transformation in nine steps. The total highlighted a one-pot stepwise synthesis involving (i) ring formation chiral epoxide, (ii) reduction alkyne, (iii) global deprotection, (iv) formation, which performed the final step synthesis.

Language: Английский

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