Total Synthesis of (±)-Ginkgolide B
Citations Over TimeTop 10% of 1999 papers
Abstract
The total synthesis of the potent PAF antagonist ginkgolide B has been accomplished. The complex\narchitecture of ginkgolide B which includes six rings, eleven stereogenic centers, ten oxygenated carbons, and\nfour contiguous fully substituted carbons is a daunting challenge for chemical synthesis. The synthesis of\nginkgolide B was accomplished through a stereoselective intramolecular photocycloaddition of enone <b>5</b> to\nconstruct the congested core of the molecule. The photocycloaddition substrate was prepared through technology\nfor the construction of carboalkoxycyclopentenones previously reported from these laboratories. Regioselective\ncyclobutane fragmentation and further functionalization of the photoadduct <b>4</b> provided the key pentacyclic\nintermediate. Acid-catalyzed rearrangement and epoxide opening were key transformations in the production\nof ginkgolide B from the pentacyclic intermediate.
Related Papers
- → Do Altmetrics Work? Twitter and Ten Other Social Web Services(2013)898 cited
- → Appearance-preserving simplification(1998)398 cited
- → An Introduction to Altmetrics(2014)115 cited
- From attention to citation: What are altmetrics and how do they work?(2014)
- Susquehanna Chorale Spring Concert "Roots and Wings"(2017)