Enantioselective synthesis and absolute configurations of aculeatins A, B, D, and 6- epi-aculeatin D

• Published in: Tetrahedron Vol. 62; no. 41; pp. 9641 - 9649
• Main Authors: Álvarez-Bercedo, Paula, Falomir, Eva, Carda, Miguel, Marco, J.A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.10.2006; Elsevier
• Subjects: Absolute configuration; Aculeatins; Aldol reaction; Asymmetric allylation; Chemistry; Chemistry, Organic; Hypervalent iodine; Oxidative spiroacetalization; Physical Sciences; Remote induction; Science & Technology; Spiroacetals; Aculeatins; Aldol reaction; Remote induction; Absolute configuration; Asymmetric allylation; Hypervalent iodine; Spiroacetals; Oxidative spiroacetalization; hypervalent iodine; aldol reaction; AMOMUM-ACULEATUM; REAGENTS; spiroacetals; NATURAL-PRODUCTS; ALDOL REACTIONS; IODINE; asymmetric allylation; oxidative spiroacetalization; KETONES; aculeatins; MARINE MACROLIDES; CHEMISTRY; remote induction; (+)-DISCODERMOLIDE; absolute configuration; DIRECTIONS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2006.07.076

The three naturally occurring, bioactive spiroacetals aculeatins A, B, and D, as well as the non-natural 6- epi-aculeatin D have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further key step was a stereoselective aldol reaction with remote induction. The absolute configurations of the natural products have been established and an erroneous structural assignment has been corrected. [Display omitted]