Cyclohexane Epoxides − Chemistry and Biochemistry of (+)-Cyclophellitol

Marco‐Contelles, José

doi:10.1002/1099-0690(200105)2001:9<1607::aid-ejoc1607>3.0.co;2-6

Cited by 39 publications

(6 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[123,124] As an example, the gold-and silver-promoted reactions between pentynoic or hexynoic acid derivatives 108 and N-(2-aminophenyl)-functionalized indoles by 1,2-or 1,3-acyloxy migrations. [125][126][127][128] After the first work by Zhang in 2005, [129] other research groups studied the reactivity of indoles and propargylic esters under gold catalysis conditions in both intra-and intermolecular processes. Very recently, Shi and co-workers prepared a series of indoles 110, N-substituted with propargylic ester systems, that were able to undergo tandem gold-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition to afford a series of polycyclic indolines 111, each containing four contiguous stereocenters (Scheme 44).…”

Section: Initiated By Carbo-or Heterocyclizationmentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

View full text Add to dashboard Cite

This review summarizes the progress achieved in the last fifteen years by application of homogeneous gold catalysis in the field of indole functionalization. Several electrophilic species obtained through gold‐catalyzed π‐activation have in fact been found to react with the nucleophilic positions of indole, thus allowing its efficient manipulation. In order to furnish a complete and clear overview on the role of the catalyst, the review is organized from the perspective of the gold‐activated substrate that is reacting with the indole. In addition, in view of the ability of gold to catalyze tandem and cascade reactions, a separate section describes tandem/cascade protocols useful for the synthesis of complex polycyclic indole derivatives. Finally, gold catalysis has also been employed for the synthesis of indole‐based natural products. For this reason, a dedicated section collects all the work in which the key step to obtain these complex indoles is represented by a gold‐catalyzed reaction.

show abstract

Section: Initiated By Carbo-or Heterocyclizationmentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…Among them were epoxides [62,63] such as cyclophellitol (isolated from Phellinus sp.) [64][65][66][67][68] (5, Figure 3), cyclohexene derivatives such as MK7607 (isolated from Curvularia eragrostidis) [69] (6, Figure 3), streptol (isolated from Streptomyces sp.) [70,71] (7, Figure 3), pericosines A-E (isolated from Periconia byssoides) (8-14, Figure 4) [72,73], carbonyl compounds such as the gabosine family (isolated from various Streptomyces strains) [74][75][76] (15-28, Figure 5), COTC (isolated from Streptomyces griseosporeus) [77] (29, Figure 5), and valienone (isolated from Streptomyces lincolnensis) [71] (30, Figure 5).…”

Section: Natural Carbapyranosesmentioning

confidence: 99%

Biosynthesis and Biological Activity of Carbasugars

Roscales

Plumet

2016

International Journal of Carbohydrate Chemistry

View full text Add to dashboard Cite

The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland's group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.

show abstract

“…C 7 -cyclitols are an important category of natural products possessing a broad spectrum of biological activities, so that a lot of natural C 7 -cyclitols and their derivatives have become the targets of organic synthesis due to these attractive biological properties . (+)-Streptol [also known as (+)-valienol, 1 in Figure ] and (−)-1- epi -streptol [or (−)-1- epi -valienol, 2 in Figure ] are two members of C 7 -cyclitols.…”

Section: Introductionmentioning

confidence: 99%

Novel Stereoselective Syntheses of (+)-Streptol and (−)-1-epi-Streptol Starting from Naturally Abundant (−)-Shikimic Acid

et al. 2021

View full text Add to dashboard Cite

Novel highly stereoselective syntheses of (+)-streptol and (−)-1-epi-streptol starting from naturally abundant (−)-shikimic acid were described in this article. (−)-Shikimic acid was first converted to the common key intermediate by 11 steps in 40% yield. It was then converted to (+)-streptol by three steps in 72% yield, and it was also converted to (−)-1-epi-streptol by one step in 90% yield. In summary, (+)-streptol and (−)-1-epi-streptol were synthesized from (−)-shikimic acid by 14 and 12 steps in 29 and 36% overall yields, respectively.

show abstract

Cyclohexane Epoxides − Chemistry and Biochemistry of (+)-Cyclophellitol

Cited by 39 publications

References 57 publications

Gold‐Catalyzed Functionalization Reactions of Indole

Gold‐Catalyzed Functionalization Reactions of Indole

Biosynthesis and Biological Activity of Carbasugars

Novel Stereoselective Syntheses of (+)-Streptol and (−)-1-epi-Streptol Starting from Naturally Abundant (−)-Shikimic Acid

Contact Info

Product

Resources

About