Stereoretentive Suzuki−Miyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to (−)-Peridinin

• Published in: Journal of the American Chemical Society Vol. 132; no. 20; pp. 6941 - 6943
• Main Authors: Woerly, Eric M, Cherney, Alan H, Davis, Erin K, Burke, Martin D
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 26.05.2010; Amer Chemical Soc
• Subjects: Alkadienes - chemistry; Carotenoids - chemical synthesis; Carotenoids - chemistry; Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; Stereoisomerism; Substrate Specificity; BORONIC ACIDS; COMPLEX; LIGANDS; BUTENOLIDES; NATURAL-PRODUCTS; PERIDININ; STEREOCHEMISTRY; OXIDATIVE ADDITION; STEREOSELECTIVE SYNTHESIS; SINGLET-OXYGEN

Stimulated by the substantial challenge of synthesizing the complex and sensitive stereogenic allene-containing core of (−)-peridinin, the first stereocontrolled coupling of haloallenes with boronic acids has been achieved. This new method and the principles that emerged during its development stand...