Formal synthesis of amphidinin B

Krishna, Palakodety Radha; Anitha, Kadimi; Raju, G.S.N.

doi:10.1016/j.tet.2012.11.075

Cited by 15 publications

(5 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The hydroxy group present in 22 was protected as its TBDMS ether to obtain 23 in 92% yield . Later, saturation of the terminal double bond as well as deprotecion of the PMB group in 23 (H 2 /Pd/C/EtOAc/rt/12 h) furnished 6 in 75% yield …”

Section: Resultsmentioning

confidence: 99%

Bioinspired First Stereoselective Total Synthesis of Spinosulfate B

et al. 2019

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Bioinspired First Stereoselective Total Synthesis of Spinosulfate B

et al. 2019

View full text Add to dashboard Cite

show abstract

“…It is a linear polyketide with a chiral side‐chain at C(16) and tri‐substituted tetrahydrofuran core. Krishna et al [101] . started the synthesis of aldehyde 90.1 from geraniol for the building of C(10)−C(21) fragment 90.3 .…”

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

View full text Add to dashboard Cite

Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

show abstract

“…In 2013, an efficient, exible, highly stereoselective synthesis of amphidinin B 359 was accomplished by Krishna and coworkers. 251 Their approach for the total synthesis of amphidinin B involved some important named reactions such as Sharpless asymmetric epoxidation, Evans' aldol, Julia olenation, oxa-Michael, Keck allylation, Mannich reaction, Evans' asymmetric alkylation, and Yamaguchi esterication. The C 1 -C 9 365 segment in amphidinin B was provided in nine steps, starting from mono-PMB ether of 1,4-butane diol 360.…”

Section: Scheme 34mentioning

confidence: 99%

“…Aer several steps, the desired natural product 359 was obtained (Scheme 69). 251 Bakuchiol and D 3 -2-hydroxybakuchiol 366 is a member of one family of monoterpene phenols occurring in the medicinal plant Psoralea corylifolia L. Its crude extract has been used for a long time as a Chinese traditional medicine. 254 For its total synthesis, 370 acts as a key intermediate reported by Xu et al 255 For the synthesis of 370 they used Evans' asymmetric alkylation of 367 with 369 giving the desired intermediate 369 in 66-68% yield with excellent diastereoselectivity (>20 : 1).…”

Section: Scheme 34mentioning

confidence: 99%