158761-02-5Relevant articles and documents
Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid
Suzuki, Yoshikazu,Nishimaki, Ryoko,Ishikawa, Makoto,Murata, Takeshi,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 7835 - 7838 (1999)
Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.
Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid
Suzuki,Nishimaki,Ishikawa,Murata,Takao,Tadano
, p. 8595 - 8607 (2000)
We have achieved the total synthesis of (-)-mniopetal E, a drimane sesquiterpenoid which inhibits the reverse transcriptase of human immunodeficiency virus (HIV)-1. Our enantiospecific total synthesis of this target molecule in naturally occurring form commenced with a known 2,3-anhydro-D-arabinitol derivative, which was prepared using the Sharpless asymmetric epoxidation strategy. The key steps of our total synthesis were as follows: (1) a combination of highly stereocontrolled inter- and intramolecular Horner-Emmons carbon elongations for construction of a butenolide tethering a 1,2,4,9-functionalized nona-5,7-diene moiety at the β-carbon, (2) stereoselective thermal intramolecular Diels-Alder reaction of the thus-formed trienic compound, providing preferentially an endo-cycloadduct with the desired π-facial selection, and (3) efficient transformation of the γ-lactone moiety in the major cycloadduct to the γ-hydroxy-γ-lactone part in mniopetal E. Our total synthesis of (-)-mniopetal E established the unsettled absolute stereochemistry of the antibiotic.
Synthetic studies towards mniopetals (II). A short synthesis of Mniopetal E
Jauch
, p. 87 - 89 (2007/10/03)
A short total synthesis of Mniopetal E in thirteen steps is reported. Key steps are a new and highly diastereoselective lithium phenylselenide induced Baylis-Hillman reaction with Feringa's butenolide, an endo-selective intramolecular Diels-Alder reaction (IMDA) and a new variant of the Parikh-Doering oxidation.
