101331-92-4Relevant academic research and scientific papers
A facile approach for the total synthesis of neurotrophic diyne tetraol petrosiol A and petrosiol E
Gangadhar, Pamarthi,Sathish Reddy,Srihari, Pabbaraja
, p. 5807 - 5817 (2016)
The first total synthesis of neurotrophic diacetylenic tetraol, petrosiol A and stereoselective total synthesis of petrosiol E was accomplished. The total synthesis involves Cadiot-Chodkiewicz coupling reaction as the key step for petrosiol A. The diastereorich chiral alcohol (third chiral center) was synthesized from CBS mediated stereoselective ketone reduction reaction for petrosiol E. Of the three chiral centers, the two chiral centers are originated from (+)-diethyl L-tartrate and the third chiral center was generated by an addition reaction of lithium trimethylsilylacetylide leading to two diastereomers which were used for the synthesis of both the natural products and their diastereomer C6-epi-petrosiol A and C6-epi-petrosiol E, respectively.
A convergent approach for the total synthesis of the α-glucosidase inhibitor (-)-panaxjapyne-C
Sathish Reddy,Gangadhar,Srihari
, p. 1524 - 1530 (2013)
The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers l-(+)-diethyltartrate and d-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps.
First total synthesis of neurotrophic diacetylene tetrol (-)-petrosiol D
Sathish Reddy,Srihari
, p. 6370 - 6372 (2013)
The first total synthesis of the natural product (-)-petrosiol D has been achieved in a linear fashion. Sharpless asymmetric epoxidation, base induced elimination reaction for the formation of chiral propargyl alcohol and Cadiot-Chodkiewicz coupling react
Toward the stereoselective synthesis of C1-C23 fragment of spirastrellolide B
Akkapalli, Rajesh,Sharma, Gangavaram V.M.,Damera, Krishna
, p. 4067 - 4070 (2014)
A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirastrellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety.
Toward the stereoselective synthesis of C1-C23 fragment of spirastrellolide B
Rajesh, Akkapalli,Sharma, Gangavaram V.M.,Damera, Krishna
, p. 4067 - 4070 (2015/02/02)
A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirastrellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety.
Investigation of diastereoselective acyclic α-alkoxydithioacetal substitutions involving thiacarbenium intermediates
Prvost, Michel,Dostie, Starr,Waltz, Marie-ve,Guindon, Yvan
, p. 10504 - 10525 (2015/02/19)
Reported herein is an experimental and theoretical study that elucidates why silylated nucleobase additions to acyclic α-alkoxythiacarbenium intermediates proceed with high 1,2-syn stereocontrol (anti-Felkin-Anh), which is opposite to what would be expected with corresponding activated aldehydes. The acyclic thioaminals formed undergo intramolecular cyclizations to provide nucleoside analogues with anticancer and antiviral properties. The factors influencing the selectivity of the substitution reaction have been examined thoroughly. Halothioether species initially form, ionize in the presence (low dielectric media) or absence (higher dielectric media) of the nucleophile, and react through SN2-like transition structures (TS A and D), where the α-alkoxy group is gauche to the thioether moiety. An important, and perhaps counterintuitive, observation in this work was that calculations done in the gas phase or low dielectric media (toluene) are essential to locate the product- and rate-determining transition structures (C-N bond formation) that allow the most reasonable prediction of selectivity and isotope effects for more polar solvents (THF, MeCN). The ΔΔG? (GTSA-TSD) obtained in silico are consistent with the preferential formation of 1,2-syn product and with the trends of stereocontrol displayed by 2,3-anti and 2,3-syn α,β-bis-alkoxydithioacetals.
Assembly of the southern macrocyclic half of (+)-spirastrellolide a through cyclic acetal tethered ring-closing metathesis and 1,3-anti-mukaiyama-aldol
Tang, Yu,Yang, Jin-Haek,Liu, Jia,Wang, Chao-Chao,Lv, Ming-Can,Wu, Yi-Biao,Yu, Xue-Liang,Ko, Changhong,Hsung, Richard P.
, p. 565 - 598 (2013/08/23)
We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered
Baylis-Hillman reaction based flexible strategy for the synthesis of gabosine I, gabosine G, epi-gabosine i and carba l-pentose
Radha Krishna, Palakodety,Kadiyala, Raghu Ram
scheme or table, p. 744 - 747 (2012/03/08)
A combination of diastereoselective Baylis-Hillman reaction and RCM reaction set is used as the flexible strategy for the ready access to cyclohexenoid and cyclopentenoid skeletons.
Efficient synthesis of the C1-C9 fragment of 7,8-O-isopropylidene protected iriomoteolide 3a derivative
Chang, Ching-Yao
scheme or table, p. 31 - 34 (2011/11/06)
An efficient and stereoselective synthesis of the C1-C9 moiety of the 7,8-O-isopropylidene protected iriomoteolide 3a derivative has been accomplished. In our strategy, we employed olefin cross-metathesis of the L-(+)-tartaric acid derivative (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl) methoxy)(tert-butyl) diphenylsilane with a synthesized methyl (S)-3-methylhex-5-enate to successfully provide the correct olefin geometry of the desired fragment.
Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone
Gan, Feng-Feng,Yang, Shao-Bo,Luo, Yong-Chun,Yang, Wan-Bang,Xu, Peng-Fei
supporting information; experimental part, p. 2737 - 2740 (2010/07/08)
A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to intro
