137664-72-3Relevant academic research and scientific papers
Total synthesis of (+)-calyculin A and (-)-calyculin B: Asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit
Smith III, Amos B.,Friestad, Gregory K.,Barbosa, Joseph,Bertounesque, Emmanuel,Hull, Kenneth G.,Iwashima, Makoto,Qiu, Yuping,Salvatore, Brian A.,Spoors, P. Grant,Duan, James J.-W
, p. 10468 - 10477 (2007/10/03)
An asymmetric synthesis of the stereochemically fully endowed C(9-25) spiroketal fragment (+)-BC of the calyculins (1-8) is described. Highlights of the synthesis include: a highly diastereoselective IBr-induced iodocarbonate cyclization to introduce the
Iodine Monobromide (IBr) at Low Temperature: Enhanced Diastereoselectivity in Electrophilic Cyclizations of Homoallylic Carbonates
Duan, James J.-W.,Smith, Amos B.
, p. 3703 - 3711 (2007/10/02)
Iodine monobromide affords superior diastereoselectivity in low-temperature electrophilic cyclizations of homoallylic carbonates.Solvent and temperature effects and the scope and limitations of the method are discussed; optimal selectivity is obtained in
CALYCULIN SYNTHETIC STUDIES. STEREOSELECTIVE CONSTRUCTION OF THE C(14)-C(25) SPIROKETAL SUBUNIT
Smith, Amos B.,Duan, James J.-W.,Hull, Kenneth G.,Salvatore, Brian A.
, p. 4855 - 4858 (2007/10/02)
A convergent, stereocontrolled synthesis of the spiroketal fragment of calyculins A-H has been achieved.Key transformations include the novel iodine monobromide-induced iodocarbonate cyclization of (+)-19, efficient coupling of epoxide (+)-14 with the ste
