Studies toward the Asymmetric Synthesis of the Right Part of the Mycalamides

Zhong, Hua; Sohn, Jae Hak; Rawal, Viresh H.

doi:10.1021/jo0615145

Cited by 13 publications

(4 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Addition of MeMgI to 27 afforded 28 . With the availability of the precursor 28 , we proceeded for its bromonium ion initiated cyclization . Compound 28 was treated with NBS in DMSO.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epi ABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM

2010

View full text Add to dashboard Cite

A stereocontrolled approach for the construction of ABC ring systems of micrandilactone A and lancifodilactone G has been developed. The synthesis involves construction of an enantiopure functionalized cycloheptene derivative 17 through RCM of the dienol 14 prepared from the known D-mannitol-derived unsaturated ester 12. A remarkable regioselectivity during hydroboration of the cycloheptene derivative 17 was observed during its transformation to the cycloheptanone 20. RCM of the diene 24 prepared stereoselectively from 20 gave the spiro-dihydrofuran 25. The ketal unit in 25 was then converted into the carbinols 28 and 36. A bromonium ion initiated highly stereocontrolled intramolecular etherification in 28 and 37 led to the tricyclic ethers 29 and 38, respectively. Reductive removal of bromine from 29 and 38 followed by RuO(4) oxidation led to the furo-furanone derivatives 31 and 40, the C-5-epi ABC ring systems of the schisandra nortriterpenoids 1 and 2.

show abstract

“…Addition of MeMgI to 27 afforded 28 . With the availability of the precursor 28 , we proceeded for its bromonium ion initiated cyclization . Compound 28 was treated with NBS in DMSO.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epi ABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM

2010

View full text Add to dashboard Cite

show abstract

“…Lingamurthy and coworkers utilized (−)‐diethyl D‐tartrate 74 derived alcohol 75 [95] for the preparation of unnatural (−)‐lentiginosine ( ent ‐ 4 ) (Scheme 13). [96] Swern oxidation, followed by stereoselective Grignard addition, afforded secondary alcohol 76 with diastereoselectivity 9 : 1.…”

Section: Chiral Pool Approachmentioning

confidence: 99%

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Fraňová

Marchalı́n

2022

Eur J Org Chem

View full text Add to dashboard Cite

Since their discovery, polyhydroxylated indolizidines have been the focus of attention for both biologists and synthetic chemists. They are classified as iminosugar alkaloids: nitrogenbased carbohydrate mimetics that are potent inhibitors of glycosidases. Many discovered glycosidase inhibitors were found to possess biological activity, and they are therefore considered to be potential therapeutics in the treatment of various diseases such as viral infections, diabetes, or cancer. Not surprisingly, the interest in the preparation of these substances has been enormous. This review presents the latest developments in the synthesis of naturally occurring polyhydroxylated indolizidines and their synthetic enantiomers. In addition, the synthesis of several novel polyhydroxylated indolizidines, which were discovered to have inhibitory activity, is reported.

show abstract

“…Furthermore, the development of novel catalytic methods for haloetherification can provide opportunities for enantiocontrol, such as some transition‐metal catalysts for the enantioselective iodoetherification of alkenes. As shown in Scheme , lactone‐alcohol 18 readily underwent a facile selenoetherification reaction to afford bicyclic compound 19 in quantitative yield, as a 1:1 mixture of diastereomers (Scheme ) …”

Section: Formation Of the Thf Ring System In The [330]furofuranonementioning

confidence: 99%

Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Peng

Ylagan

Siu

et al. 2015

Chemistry An Asian Journal

View full text Add to dashboard Cite

The synthesis and application of [3.3.0]furofuranone species has received considerable attention from the scientific community. During the last twenty years, there has been a remarkable increase in publications focusing on their relevant method development as well as applications to natural product synthesis. This tutorial review discusses instructive examples to give a special emphasis on the development of new synthetic approaches and important applications to the total synthesis of natural products.

show abstract

Studies toward the Asymmetric Synthesis of the Right Part of the Mycalamides

Cited by 13 publications

References 58 publications

Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epi ABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM

Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epi ABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Contact Info

Product

Resources

About