TY - JOUR
T1 - Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift
AU - Yang, Zhi
AU - Li, Yi
AU - Pattenden, Gerald
N1 - Funding Information:
We thank the Chinese Government , together with Yunnan Baiyao Group Co. Ltd., Kunming, China for financial support to Dr. Z.Y.
PY - 2010/8/14
Y1 - 2010/8/14
N2 - Irradiation of a solution of synthetic Z-deoxypukalide 10 in acetonitrile (Pyrex; 400 W Hg lamp) resulted in isomerisation, leading to E-deoxypukalide 12, which was isolated recently from the octocoral Leptogorgia spp. Further irradiation of 12, or prolonged irradiation of 10, then gave the ring-contracted product, deoxypseudopterolide 1 (>90%) found in octocorals of the genera Pseudopterogorgia and Leptogorgia. The contraction of the 14-membered rings in 10 and 12 to the 12-membered ring as 1, occurs by way of photochemical [1,3]-sigmatropic rearrangement.
AB - Irradiation of a solution of synthetic Z-deoxypukalide 10 in acetonitrile (Pyrex; 400 W Hg lamp) resulted in isomerisation, leading to E-deoxypukalide 12, which was isolated recently from the octocoral Leptogorgia spp. Further irradiation of 12, or prolonged irradiation of 10, then gave the ring-contracted product, deoxypseudopterolide 1 (>90%) found in octocorals of the genera Pseudopterogorgia and Leptogorgia. The contraction of the 14-membered rings in 10 and 12 to the 12-membered ring as 1, occurs by way of photochemical [1,3]-sigmatropic rearrangement.
KW - 1,3-Allylic shift, [1,3] Sigmatropic rearrangement
KW - Deoxypseudopterolide
KW - E-Deoxypukalide
KW - Octocorals
KW - Photochemical ring contraction
UR - http://www.scopus.com/inward/record.url?scp=77955659950&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.04.001
DO - 10.1016/j.tet.2010.04.001
M3 - Article
AN - SCOPUS:77955659950
SN - 0040-4020
VL - 66
SP - 6546
EP - 6549
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -