Construction of 2,6-trans pyrans via Prins cyclization and its application towards the total synthesis of methyl sarcophytoate

• Main Author: Hu, Xuhong
• Other Authors: Yang Hua Zheng
• Format: Theses and Dissertations
• Language: English
• Published: 2012
• Subjects: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
• Online Access: https://hdl.handle.net/10356/47588
• Institution: Nanyang Technological University

Prins cyclization reaction involving a homoallylic alcohol with aldehyde is one of the most efficient methods to synthesize tetrahydropyran rings. However, due to the strong 1,3-diaxial interaction, the 2,6-cis tetrahydropyran moiety was formed preferably in most cases. The emphasis of this thesis is focused on the evolution of a convenient catalytic Prins cyclization for the construction of 2,6-trans pyranyl motifs and its application towards the total synthesis of natural product.