851616-13-2Relevant academic research and scientific papers
Alkyne-mediated approach for total syntheses of cladospolides A, B, C and iso-cladospolide B
Reddy, Chada Raji,Suman, Devatha,Rao, Nagavaram Narsimha
, p. 3786 - 3796 (2013/07/19)
A general strategy for the stereoselective total syntheses of cladospolides A, B, and C and iso-cladospolide B has been accomplished. The key steps provide easy access to the target molecules and include an alkyne-zipper reaction, a Sharpless asymmetric e
A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B
Si, Debjani,Sekar, Narayana M.,Kaliappan, Krishna P.
supporting information; experimental part, p. 6988 - 6997 (2011/11/05)
A simple, efficient and flexible strategy for the syntheses of cladospolides A-C and iso-cladospolide B is reported here. This strategy involves Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps, starting from either d-ribose or suitable tartaric acid esters. Although our initial efforts towards cladospolide A involving a ring closing metathetic approach were not successful, changing the mode of ring closure and the use of Julia-Kocienski olefination for the construction of the key intermediate solved this issue and paved the way for the completion of total syntheses of this class of natural products.
De novo asymmetric synthesis of cladospolide B-D: Structural reassignment of cladospolide D via the synthesis of its enantiomer
Xing, Yalan,O'doherty, George A.
supporting information; experimental part, p. 1107 - 1110 (2009/07/25)
The enantioselective synthesis of cladospolide B, C, and (ent)-cladospolide D has been achieved in 11-15 steps from 1-nonyne. The route relies upon an alkyne zipper reaction to relay an ynone and dienoate functional groups across a nine carbon fragment, which enables a highly enantioselective Noyori ynone reduction and a diastereo-and regioselective Sharpless dihydroxylation of a dienoate. In addition to being a flexible approach to three members of the cladospolide natural products, this route for the first time correctly established the structure for cladospolide D.
Structure investigations of (ent)-cladospolide d by de novo synthesis and kinetic and thermodynamic isomerization
Xing, Yalan,Penn, John H.,O'Doherty, George A.
scheme or table, p. 2847 - 2854 (2010/03/25)
The de novo asymmetric synthesis of cladospolides B and C and (ent)-cladospolide D has been achieved from achiral non-1-yne. The 11-13-step route relies upon a Noyori reduction and a KAPA promoted alkyne zipper reaction to relay an achiral functionality a
Attempts directed towards the synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C
Sharma,Reddy, J. Janardhan,Reddy, K. Laxmi
, p. 6531 - 6535 (2007/10/03)
Attempts to synthesise iso-cladospolide-B, cladospolide-B and cladospolide-C resulted in macrolides 1, 2 and 4 along with butenolide 3. Of the three stereogenic centres, the C-4/C-5 vic-diol was obtained from tartaric acid and d-glucose, while the C-11 st
A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide B via a mid-stage ring-closing metathesis and a late-stage photo-rearrangement of the E-isomer
Austin, Kerrie A. B.,Banwell, Martin G.,Loong, David T. J.,Rae, A. David,Willis, Anthony C.
, p. 1081 - 1088 (2007/10/03)
A sixteen-step synthesis of the twelve-membered macrolide (-)-cladospolide B (2) from the microbially-derived cis-1,2-dihydrocatechol 5 is described. Pivotal steps include the ring-closing metathesis (RCM) of diene 12 to give the ten-membered lactone 13 t
Efficient total synthesis of iso-cladospolide B and cladospolide B
Pandey, Satyendra Kumar,Kumar, Pradeep
, p. 6625 - 6627 (2007/10/03)
An efficient synthesis of iso-cladospolide B and cladospolide B has been achieved using Jacobsen's hydrolytic kinetic resolution (HKR), Sharpless asymmetric dihydroxylation and Yamaguchi macrolactonization as the key steps.
