Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F

doi:10.1016/j.tetlet.2014.12.054

. 2015 Jun 3;56(23):3225-3227.

doi: 10.1016/j.tetlet.2014.12.054.

Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F

Heping Shi¹, Saptarshi De¹, Qiaoling Wang¹, Shuanhu Gao¹, Xiao Wang¹, Chuo Chen¹

Affiliations

PMID: 26097263
PMCID: PMC4472376
DOI: 10.1016/j.tetlet.2014.12.054

Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F

Heping Shi et al. Tetrahedron Lett. 2015.

. 2015 Jun 3;56(23):3225-3227.

doi: 10.1016/j.tetlet.2014.12.054.

Authors

Heping Shi¹, Saptarshi De¹, Qiaoling Wang¹, Shuanhu Gao¹, Xiao Wang¹, Chuo Chen¹

Affiliation

¹ Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390-9038, United States.

PMID: 26097263
PMCID: PMC4472376
DOI: 10.1016/j.tetlet.2014.12.054

Abstract

We report herein the synthesis of a fully functionalized B,C,D-ring system of lancifodilactone F. The key transformations involve an arene-olefin meta-photocycloaddition reaction and a palladium-catalyzed oxidative C-C cleavage reaction to establish its B,C-rings.

Keywords: cycloaddition; oxidation; palladium; photochemistry; terpenoid.

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Figures

**Figure 1**
Structure of lancifodilactone F (1) and our synthetic strategy.

**Figure 2**
Model studies for the establishment and functionalization of the carbon skeleton of lancifodilaction F (1).

**Figure 3**
Construction of the B,C,D-ring system of lacifodilactone F (1).

See this image and copyright information in PMC

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[1] Xiao W-L, Li R-T, Li S-H, Li X-L, Sun H-D, Zheng Y-T, Wang R-R, Lu Y, Wang C, Zheng Q-T. Org. Lett. 2005;7:1263–1266. - PubMed

[2] Xiao W-L, Li R-T, Li S-H, Li X-L, Sun H-D, Zheng Y-T, Wang R-R, Lu Y, Wang C, Zheng Q-T. Org. Lett. 2005;7:1263–1266. - PubMed

[3] Xiao W-L, Li R-T, Li S-H, Li X-L, Sun H-D, Zheng Y-T, Wang R-R, Lu Y, Wang C, Zheng Q-T. Org. Lett. 2006;8:801. - PubMed

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[5] Zhang Y-D, Tang Y-F, Luo T-P, Shen J, Chen J-H, Yang Z. Org. Lett. 2006;8:107–110. - PubMed

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[8] Xiao Q, Ren W-W, Chen Z-X, Sun T-W, Li Y, Ye Q-D, Gong J-X, Meng F-K, You L, Liu Y-F, Zhao M-Z, Xu L-M, Shan Z-H, Shi Y, Tang Y-F, Chen J-H, Yang Z. Angew. Chem. Int. Ed. 2011;50:7373–7377. - PubMed

[9] Sun T-W, Ren W-W, Xiao Q, Tang Y-F, Zhang Y-D, Li Y, Meng F-K, Liu Y-F, Zhao M-Z, Xu L-M, Chen J-H, Yang Z. Chem. Asian J. 2012;7:2321–2333. - PubMed

[10] Sun T-W, Ren W-W, Xiao Q, Tang Y-F, Zhang Y-D, Li Y, Meng F-K, Liu Y-F, Zhao M-Z, Xu L-M, Chen J-H, Yang Z. Chem. Asian J. 2012;7:2321–2333. - PubMed

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Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F

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Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F

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