Diels–Alder Reactions of Masked o‐Benzoquinones with 1‐Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton. Issue 18 (9th May 2014)

• Record Type: Journal Article
• Authors: Niu, Guang‐Hao; Hou, Chieh‐Shen; Chuang, Gary Jing; Wu, Chi‐Phi; Liao, Chun‐Chen
• Is Part Of: European journal of organic chemistry. Issue 18(2014)
• Page Start: 3794
• Page End: 3801
• Publication Date: 2014-05-09
• Subjects: Synthetic methods -- Cycloaddition -- Sigmatropic rearrangement -- Polycycles -- Quinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201400016
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Masked o ‐benzoquinones (MOBs), which were generated in situ from 2‐methoxyphenols, underwent Diels–Alder reactions with 1‐vinylcyclohexenes to produce the corresponding cycloaddition products, that is, decahydrophenanthrenes along with bicyclo[2.2.2]octenones. In the former case, the MOBs serve as the dienophile, and in the later case, the 1‐vinylcyclohexenes act as the dienophile. The obtained bicyclo[2.2.2]octenones could be transformed into the corresponding decahydrophenanthrenes through a Cope rearrangement at 220 °C. Thus, these tandem reactions provide a short and efficient entry to the decahydrophenanthrene skeleton from easily available 2‐methoxyphenols. Abstract : Masked o ‐benzoquinones (MOBs), which were generated in situ from 2‐methoxyphenols, underwent Diels–Alder reactions with 1‐vinylcyclohexenes to produce the corresponding decahydrophenanthrenes and bicyclo[2.2.2]octenones. The obtained bicyclo[2.2.2]octenones could be transformed into decahydrophenanthrenes through a Cope rearrangement at 220 °C.