z-logo
Premium
Towards a Total Synthesis of Phenalinolactone Core Diterpenoid 6: Synthesis of a Racemic Decahydrobenzocyclobutaisobenzofuran with a trans‐anti‐cis Junction of the Isocyclic Rings
Author(s) -
Hampel Thomas,
Brückner Reinhard
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700198
Subject(s) - chemistry , annulation , intramolecular force , ring (chemistry) , stereochemistry , cyclohexanone , cyclohexene , cyclohexane , total synthesis , epoxide , catalysis , organic chemistry
Synthetic efforts towards the “phenalinolactone core diterpenoid 6” ( 5 ) are described. It contains a cyclohexyl alcohol (A ring), a cyclohexane (B ring), and a cyclohexene (C ring), which are angularly annulated trans and cis , respectively. What makes them unique is the trans ‐ (or “ anti ”‐) relationship between the A and the C ring. The trans ‐configured A/B ring junction was established in a novel cyclohexanone annulation. Anti ‐selective cis ‐annulations of the C ring failed when attempted with intramolecular Diels–Alder reactions with dienes of varied electron demand ( 21 , 31 ). In contrast, an anti ‐selective cis ‐annulation of a C ring precursor based on an intramolecular [2+2]‐photocycloaddition succeeded. It provided the tetracycle 38 in 70 % yield. It contains a densely functionalized four‐membered ring. It should lend itself to ring‐opening(s) and/or rearrangement(s). Accordingly, compound 38 should be adoptable to proceeding to the target structure 5 in future work.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom