Total Synthesis of Leucascandrolide A:  A New Application of the Mukaiyama Aldol−Prins Reaction

Orden, L. J. Van; Patterson, Brian D.; Rychnovsky, Scott D.

doi:10.1021/jo070901r

Cited by 61 publications

(10 citation statements)

References 50 publications

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“…Finally, we considered the use of C-nucleophiles in substitution reactions with pyridinium-type salts that were derived from THP and other related esters. [18][19][20][21] The 2-p-tolylpyridinium salt of compound 4 did not react with the Gilman reagent (Ph 2 CuLi), which was previously observed to participate in similar alkylation reactions of acetals ( Table 6, entry 1). [6] Phenyl lithium and phenyl magnesium bromide also did not react to yield substitution products ( Table 6, entries 2 and 3).…”

Section: Use Of C-nucleophilesmentioning

confidence: 81%

Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

Fujioka

Minamitsuji

Moriya

et al. 2012

Chemistry An Asian Journal

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Nucleophilic substitution at the anomeric positions of tetrahydropyranyl (THP) and related carbohydrate-derived esters that proceeded through pyridinium-type salt intermediates have been developed. Treatment of the 6-substituted α-acetoxy-tetrahydropyrans with TMSOTf (TMS=trimethylsilyl) and 2-substitutited pyridines, such as 2-p-tolylpyridine and 2-methoxypyridine, led to the efficient generation of cis-pyridinium-type salts. These salts reacted with various nucleophiles, such as alcohols, azides, and organozinc reagents, to form nucleophilic-substitution products. A characteristic feature of these processes was that they took place under mild conditions, which did not affect acid-labile protecting groups. Furthermore, the reactions that employed azides and C-nucleophiles generated 2,6-trans products with high degrees of stereoselectivity.

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Section: Use Of C-nucleophilesmentioning

confidence: 81%

Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

Fujioka

Minamitsuji

Moriya

et al. 2012

Chemistry An Asian Journal

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“…This approach was further extended to the synthesis of the macrolide lecasacandrolide A [ 41 ]. BF 3 ·OEt 2 in combination with 2,6-di- tert -butylpyridine (DTBP) was a suitable combination for the synthesis of the THP unit of leucasacandrolide A, while TiBr 4 [ 42 ] was found suitable in conjunction with DTBP for the synthesis of polyketide SCH 351448 [ 43 ], as shown in Scheme 14 .…”

Section: Reviewmentioning

confidence: 99%

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

Budakoti

Mondal

Verma

et al. 2021

Beilstein J. Org. Chem.

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Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous scaffolds in many natural products and active pharmaceutical ingredients (API). Among various established methods, the Prins reaction has emerged as a powerful technique in the stereoselective synthesis of the tetrahydropyran skeleton with various substituents, and the strategy has further been successfully applied in the total synthesis of bioactive macrocycles and related natural products. In this context, hundreds of valuable contributions have already been made in this area, and the present review is intended to provide the systematic assortment of diverse Prins cyclization strategies, covering the literature reports of the last twenty years (from 2000 to 2019), with an aim to give an overview on exciting advancements in this area and designing new strategies for the total synthesis of related natural products.

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“…Du and co-workers [111] developed a highly efficient cyclization of (Z)-enynols in the presence of gold catalyst under mild reaction conditions (Scheme 10) [112][113][114].…”

Section: Synthesis Of Six-membered One Oxygen Containing Heterocyclesmentioning

confidence: 99%

Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles

et al. 2019

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The heterocycles are present in the drugs and pesticides in a major proportion and development of new strategies for the synthesis of these compounds is attractive topic for the synthetic and medicinal chemists. Synthesis of heterocycles is one of the important areas in synthetic organic chemistry. The present manuscript reported the synthesis of six-membered heterocylces with oxygen heteroatom using gold catalysts. This review covered interesting discoveries in the past few years.

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Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol−Prins Reaction

Cited by 61 publications

References 50 publications

Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles

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