Tandem Prins Cyclization for the Stereoselective Synthesis of Bridged Benzopyran Derivatives

• Published in: Asian journal of organic chemistry Vol. 5; no. 8; pp. 1068 - 1072
• Main Authors: Subba Reddy, Basi V., Srivastava, Nikhil, Begum, Zubeda, Lakshmi, Jerripothula K., Sridhar, Balasubramanian
• Format: Journal Article
• Language: English
• Published: Weinheim Blackwell Publishing Ltd 01-08-2016; Wiley Subscription Services, Inc
• Subjects: aldehydes; benzopyrans; Lewis acids; Organic chemistry; Prins cyclization; synthetic methods
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201600196

A tandem bicyclization strategy has been developed for the stereoselective synthesis of 3,4‐dihydro‐2 H,6H‐2,6‐methanobenzo[b][1,5]dioxocine derivatives in good yields and selectivities through the cyclocondensation of 2‐(1‐hydroxy‐3‐methylbut‐3‐en‐1‐yl)phenol with various aldehydes by using 10 mol % BF3⋅OEt2. This is the first reported stereoselective construction of a bridged tricyclic skeleton through a cascade Prins cyclization procedure. This process constitutes an elegant strategy for the quick construction of tricyclic architectures in a single step.
Prins of thieves: A tandem strategy has been developed for the stereoselective synthesis of 3,4‐dihydro‐2 H,6 H‐2,6‐methanobenzo[b][1,5]dioxocine derivatives in good yields.