TY - JOUR
T1 - Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.
AU - Tang, Bencan
AU - Bray, Christopher D.
AU - Pattenden, Gerald
AU - Rogers, Joseph
N1 - Funding Information:
We thank the University of Nottingham for a Dorothy Hodgkin Postgraduate-Hutchinson Whampoa Award (to B.T.) and for a Fellowship (to C.D.B.). We also thank the EPSRC for a postgraduate studentship (to J.R.) and Merck Sharp and Dohme for financial support.
PY - 2010/3/27
Y1 - 2010/3/27
N2 - A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals.
AB - A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals.
UR - http://www.scopus.com/inward/record.url?scp=77349111714&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.01.059
DO - 10.1016/j.tet.2010.01.059
M3 - Article
AN - SCOPUS:77349111714
SN - 0040-4020
VL - 66
SP - 2492
EP - 2500
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -
