TY - JOUR
T1 - Applications of crotyldiisopinocampheylboranes in synthesis
T2 - A formal total synthesis of (+)-calyculin A
AU - Anderson, Oren P.
AU - Barrett, Anthony G.M.
AU - Edmunds, Jeremy J.
AU - Hachiya, Shun Ichiro
AU - Hendrix, James A.
AU - Horita, Kiyoshi
AU - Malecha, James W.
AU - Parkinson, Christopher J.
AU - Vansickle, Andrew
PY - 2001
Y1 - 2001
N2 - The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.
AB - The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.
KW - Aldol reactions
KW - Allylboration reactions
KW - Calyculin
KW - Cornforth-Meyers oxazole reaction
KW - Marine natural product
KW - Palladium catalyzed coupling reactions
KW - Phosphatase inhibitor
KW - Spiroketal
KW - Total synthesis
UR - https://www.scopus.com/pages/publications/0035681095
UR - https://www.scopus.com/pages/publications/0035681095#tab=citedBy
U2 - 10.1139/cjc-79-11-1562
DO - 10.1139/cjc-79-11-1562
M3 - Article
AN - SCOPUS:0035681095
SN - 0008-4042
VL - 79
SP - 1562
EP - 1592
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
IS - 11
ER -