1219715-21-5Relevant articles and documents
Total Synthesis and Structural Revision of Monocillin VII
Mallampudi, N. Arjunreddy,Srinivas, Beduru,Reddy, Jithender G.,Mohapatra, Debendra K.
, p. 5952 - 5956 (2019)
The first asymmetric total synthesis of macrolactone monocillin VII and its C-10′ epimer was achieved starting from a known chiral pure epoxide in 16 longest linear sequences. The present synthesis highlights the macrolactone formation involving an alkyne-dicobalt carbonyl complex under De Brabander's conditions followed by an unexpected regioselective hydration. The asymmetric total synthesis resulted in the revision of the configuration at C10′ and reassignment of the absolute configuration of the natural product.
CuBr2-catalyzed diastereoselective allylation: Total synthesis of decytospolides A and B and their C6-epimers
Choudhury, Utkal Mani,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.,Padhi, Birakishore,Reddy, G. Sudhakar
, p. 2685 - 2695 (2020/04/17)
An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.
Total Synthesis of Four Isomers of the Proposed Structures of Cryptorigidifoliol K
Reddy, G. Sudhakar,Padhi, Birakishore,Bharath, Yada,Mohapatra, Debendra K.
supporting information, p. 6506 - 6509 (2017/12/26)
The first asymmetric convergent total synthesis of four isomers of proposed structures of cryptorigidifoliol K (1a, 1b, 1c, and 1d) has been achieved from commercially available starting materials. The key steps in this synthesis involve tandem isomerization followed by a C-O and C-C bond-forming reaction for the construction of trans-2,6-disubstituted dihydropyran, iodolactonization, isomerization of terminal alkene, and cross-metathesis reaction. The large discrepancies in the spectroscopic data (1H NMR) of synthetic cryptorigidifoliol K from the natural product suggest that the structure of the natural cryptorigidifoliol K requires revision.
Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: Application to concise construction of C28-C37 bicyclic core of (H-)-sorangicin A
Mohapatra, Debendra K.,Das, Pragna P.,Pattanayak, Manas Ranjan,Yadav
experimental part, p. 2072 - 2078 (2010/07/05)
A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6disubstituted-3,4-dihydropyrans have been achieved from o-hydroxy-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21 % overall yield.
