Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift

Zhi Yang; Yi Li; Gerald Pattenden

doi:10.1016/j.tet.2010.04.001

Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift

Zhi Yang
, Yi Li
, Gerald Pattenden^*

^*Corresponding author for this work

University of Nottingham

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	6546-6549
Number of pages	4
Journal	Tetrahedron
Volume	66
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2010.04.001
Publication status	Published - 14 Aug 2010
Externally published	Yes

Keywords

1,3-Allylic shift, [1,3] Sigmatropic rearrangement
Deoxypseudopterolide
E-Deoxypukalide
Octocorals
Photochemical ring contraction

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10.1016/j.tet.2010.04.001

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@article{cf03beac4eef4eaa91cff8a356ce5b12,

title = "Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift",

abstract = "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.",

keywords = "1,3-Allylic shift, [1,3] Sigmatropic rearrangement, Deoxypseudopterolide, E-Deoxypukalide, Octocorals, Photochemical ring contraction",

author = "Zhi Yang and Yi Li and Gerald Pattenden",

note = "Funding Information: We thank the Chinese Government , together with Yunnan Baiyao Group Co. Ltd., Kunming, China for financial support to Dr. Z.Y. ",

year = "2010",

month = aug,

day = "14",

doi = "10.1016/j.tet.2010.04.001",

language = "English",

volume = "66",

pages = "6546--6549",

journal = "Tetrahedron",

issn = "0040-4020",

number = "33",

}

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 - https://www.scopus.com/pages/publications/77955659950

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 -

Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift

Abstract

Keywords

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