- Total synthesis of (–)-cephalosporolide D
-
In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.
- Kalavakuntla, Chiranjeevi,Kummari, Vijaya Babu,Yadav, Jhillu Singh
-
supporting information
(2021/03/22)
-
- Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits
-
Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.
- Crimmins, Michael T.,Ellis, J. Michael,Emmitte, Kyle A.,Haile, Pamela A.,McDougall, Patrick J.,Parrish, Jonathan D.,Zuccarello, J. Lucas
-
scheme or table
p. 9223 - 9234
(2010/04/25)
-
- Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A
-
(Chemical Equation Presented) A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
- Crimmins, Michael T.,Zuccarello, J. Lucas,Cleary, Pamela A.,Parrish, Jonathan D.
-
p. 159 - 162
(2007/10/03)
-
- A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis
-
A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.
- Kadota, Isao,Uyehara, Hiroshi,Yamamoto, Yoshinori
-
p. 7361 - 7365
(2007/10/03)
-