Synthesis of Unsaturated Trans-Fused Polyether Frameworks via O-linked Oxacycles: A Convergent Approach

Álvarez, Eleuterio; Diaz, M. T.; Liu, Hanxing; Martı́n, Julio D.

doi:10.1021/ja00109a032

Cited by 44 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3). 21 This pioneering work was extended to convergent methodologies to assemble polycyclic ethers by Martín 22 and Tachibana. 23 In studies toward the total synthesis of ciguatoxin, Tachibana and co-workers developed a method for the synthesis of 6/9/6-tricyclic system in 1997.…”

Section: Nucleophilic Addition Of -Alkoxyallylsilane To Cyclic Acetalmentioning

confidence: 99%

Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates

Inoue

2004

Org. Biomol. Chem.

View full text Add to dashboard Cite

One of the most characteristic and spectacular class of compounds isolated from marine sources is the polycyclic ethers. Following the initial report of the structural determination of brevetoxin B, a variety of novel polycyclic ethers have begun to surface. These natural products include ciguatoxins, gambierol, gambieric acids, yessotoxins and gymnocins, each of which exhibit distinct biological properties such as cytotoxicity and neurotoxicity, as well as antiviral and antifungal activities. Because of these intriguing biological activities and their complex molecular architecture, the total synthesis of these compounds has been pursued by many laboratories over two decades. In particular, the development of novel convergent strategies to assemble the structural fragments is crucial for the successful construction of these nano-scale molecules. This Perspective will focus on a recent convergent methodology using an acetal-linkage as a key motif. Application of this methodology culminated in the total syntheses of gambierol and ciguatoxin CTX3C.

show abstract

Section: Nucleophilic Addition Of -Alkoxyallylsilane To Cyclic Acetalmentioning

confidence: 99%

Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates

Inoue

2004

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…The reaction of the allylic stannane 32 having a tetrahydropyran ring on the acetal moiety with TiCl 3 (O i Pr) gave 33 as the predominant product in 73% yield (Scheme 9). 24 The product 33 was converted to the tricyclic ether 34 via the thioether formation and desulfo-olefination. Unfortunately, the stereochemistry of the product 34 through this ring fusion does not correspond to that of natural polycyclic ethers.…”

Section: Convergent Synthesis Via the Intramolecular Allylation Of R-mentioning

confidence: 99%

Synthetic Strategies of Marine Polycyclic Ethers via Intramolecular Allylations: Linear and Convergent Approaches

Kadota

Yamamoto

2005

Acc. Chem. Res.

View full text Add to dashboard Cite

Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of alpha-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

show abstract

“…Recent examples from other groups, shown in Fig. 1, include a formal total synthesis of brassinolide, 6 the total syntheses of (+)-solamin, 7 (+)-eremantholide A 8 and (2)-conduritol E derivatives, 9 the preparation of enediyne 10 and ciguatoxin 11 analogues, and the synthesis of an advanced intermediate to the C-aryl glycoside chrysomycin A. 12 In terms of the mechanism of the Ramberg-Bäcklund reaction, considerable progress was made in the 1950s and 1960s.…”

Section: (A) Introductionmentioning

confidence: 99%

Recent developments in Ramberg–Bäcklund and episulfone chemistry

Taylor¹

1999

Chem. Commun.

View full text Add to dashboard Cite

Synthesis of Unsaturated Trans-Fused Polyether Frameworks via O-linked Oxacycles: A Convergent Approach

Cited by 44 publications

References 0 publications

Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates

Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates

Synthetic Strategies of Marine Polycyclic Ethers via Intramolecular Allylations: Linear and Convergent Approaches

Recent developments in Ramberg–Bäcklund and episulfone chemistry

Contact Info

Product

Resources

About