An enantiodivergent protocol from R-(-)-carvone: synthesis of dihydroagarofuran sesquiterpenoid 1-deacetoxy-ent-orbiculin A

作者：Kumaran R Senthil; Mehta Goverdhan^*

来源：Tetrahedron, 2015, 71(10): 1547-1554.

DOI：10.1016/j.tet.2015.01.033

• Sesquiterpenoids
• Enantiodivergent synthesis
• Dihydroagarofurans
• Ring closure metathesis
• Rubottom oxidation

A strategy for achieving enantiodivergency from R-(-)-carvone in the context of synthesis of eudesmanes and dihydroagarofurans is disclosed, which involves, among other things, sequential setting of the C10 quaternary centre and recreation of the desired C7 isopropyl stereochemistry to enter the antipodal series. A synthesis of 1-deacetoxy-ent-orbiculin has been achieved as a demonstration of the effectiveness and applicability of this approach.

• 出版日期2015-3-11