Synthesis of verrucarin A

Still, W. Clark; Ohmizu, Hiroshi

doi:10.1021/jo00338a046

Cited by 75 publications

(17 citation statements)

References 3 publications

(3 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…0018-019X/82/5/1412-06$01.00/0 synthesis of a naturally occurring macrocyclic trichothecane ester, verrucarin A (4), was reported very recently by Still et al [9]. The latter communication prompts us to disclose briefly our own results, by which not only the synthesis of verrucarin A (4) but also of 3 a-hydroxyverrucarin A (5) has been successfully completed.…”

Section: Discussionmentioning

confidence: 61%

“…One of these focussed on the cyclization of a seco-acid containing a (Z)-enoic group with the secondary 4-hydroxy group of verrucarol (2). The other approach, which is described in this communication in more detail, uses a similar strategy to that applied in the meantime by Still et al [9]. The first idea seemed attractive because of the ready availability of the required (Z/E)-muconic half ester 10.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Verrucarin A and 3α‐Hydroxyverrucarin A from Verrucarol and Diacetoxyscripenol (Anguidine). 39th Communication on Verrucarins and Roridins

Mohr

Tori

Grossen

et al. 1982

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

Section: Discussionmentioning

confidence: 61%

Section: Discussionmentioning

confidence: 99%

Synthesis of Verrucarin A and 3α‐Hydroxyverrucarin A from Verrucarol and Diacetoxyscripenol (Anguidine). 39th Communication on Verrucarins and Roridins

Mohr

Tori

Grossen

et al. 1982

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…Silylation of homopropargylic alcohol 9 and trapping of the corresponding acetylide with formaldehyde gave propargylic alcohol 10 in 71 % overall yield. Partial hydrogenation9 of 10 with Lindlar catalyst gave the corresponding Z allylic alcohol (98 % yield), which was subjected to Sharpless asymmetric epoxidation conditions to yield epoxy alcohol 11 in almost quantitative yield (99 %). Compound 11 was then oxidized to the corresponding epoxy acid (80 % yield), which was subsequently treated with AlMe 3 9 at ambient temperature to afford, upon methylation with MeI, hydroxyester 12 as a single isomer in 72 % overall yield for the two steps.…”

Section: Methodsmentioning

confidence: 99%

“…Partial hydrogenation9 of 10 with Lindlar catalyst gave the corresponding Z allylic alcohol (98 % yield), which was subjected to Sharpless asymmetric epoxidation conditions to yield epoxy alcohol 11 in almost quantitative yield (99 %). Compound 11 was then oxidized to the corresponding epoxy acid (80 % yield), which was subsequently treated with AlMe 3 9 at ambient temperature to afford, upon methylation with MeI, hydroxyester 12 as a single isomer in 72 % overall yield for the two steps. Treatment of 12 with triflic anhydride, followed by exposure of the resulting triflate to sodium azide furnished, with inversion of configuration, the orthogonally protected isoleucine derivative 13 in 75 % overall yield.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of Halipeptins A and D and Analogues

et al. 2005

View full text Add to dashboard Cite

Trügerische Ringe: Die Halipeptine A (1 a) und D (1 b) und einige ihrer Analoga wurden aus den Fragmenten 2 und 3 a bzw. 3 b synthetisiert. Zu den Schlüsselschritten zählten die Bildung von Peptidbindungen, ein DAST‐vermittelter Thiazolin‐Aufbau und eine Makrolactamisierung. Im Unterschied zu (möglicherweise verunreinigtem) Material aus natürlichen Quellen war synthetisches 1 b nur schwach wirksam gegen Tumorzellen. DAST=(Diethylamino)schwefeltrifluorid.

show abstract

“…Oxidation of a 2,3-epoxy alcohol to the corresponding acid was effected by RuCl 3 /aq. Na(IO 4 )/CCl 4 -CH 3 CN during the synthesis of the naturally occurring toxin verrucarin A [129]. The reagent TPAP/NMO/PMS/CH 2 Cl 2 was used to make the immunosuppressive agent antascomicin B [130], and a step in the synthesis of the microbial metabolite (+)-SCH 351448 involved oxidation of a primary alcohol to an acid also used the reagent [131].…”

Section: Model Substratesmentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

View full text Add to dashboard Cite

This is one of the most important classes of oxidation effected by Ru complexes, particularly by RuO 4 , [RuO 4 ] − , [RuO 4 ] 2− and RuCl 2 (PPh 3 ) 3 , though in fact most Ru oxidants effect these transformations. The chapter covers oxidation of primary alcohols to aldehydes (section 2.1), and to carboxylic acids (2.2), and of secondary alcohols to ketones (2.3). Oxidation of primary and secondary alcohol functionalities in carbohydrates (sugars) is dealt with in section 2.4, then oxidation of diols and polyols to lactones and acids (2.5). Finally there is a short section on miscellaneous alcohol oxidations in section 2.6.In this chapter the first of the two most important categories of oxidations catalysed by Ru complexes (the other being alkene and alkyne oxidations in Chapter 3) are considered. The approach in this and subsequent chapters differs from that of Chapter 1, concentrating here on the substrate rather than on the oxidant. The text is divided into the categories of alcohols and their oxidations. There are summaries in section 2.3.6 of systems of limited applicability which are mentioned only in Chapter 1, and in section 2.3.7 of large-scale (>1 g) oxidations.The first oxidations of alcohols by stoicheiometric RuO 4 /H 2 O were reported in 1958, of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones [1]. The first Ru-catalysed oxidation of an alcohol was reported in 1965 when Parikh and Jones used RuO 2 /aq. Na(IO 4 )/CCl 4 1 ( Table 2.3) [2] to oxidise secondary alcohol groups in carbohydrates.Oxidation of alcohols is the most frequently reviewed topic for Ru-catalysed oxidations [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Mechanisms of alcohol oxidation by Ru complexes have been reviewed [21].

show abstract

Synthesis of verrucarin A

Cited by 75 publications

References 3 publications

Synthesis of Verrucarin A and 3α‐Hydroxyverrucarin A from Verrucarol and Diacetoxyscripenol (Anguidine). 39th Communication on Verrucarins and Roridins

Synthesis of Verrucarin A and 3α‐Hydroxyverrucarin A from Verrucarol and Diacetoxyscripenol (Anguidine). 39th Communication on Verrucarins and Roridins

Total Synthesis of Halipeptins A and D and Analogues

Oxidation of Alcohols, Carbohydrates and Diols

Contact Info

Product

Resources

About