Enantioselective Synthesis of the G-Ring of Brevetoxin A

Crimmins, Michael T.; Cleary, Pamela A.

doi:10.3987/com-03-s46

Cited by 18 publications

(14 citation statements)

References 5 publications

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“…Most of the standard solid explosives exhibit very low vapor pressure at room temperature. − One of the highest vapor pressures corresponds to 2,4,6-trinitrotoluene (TNT), whose magnitude is about 10 –6 Torr at room temperature. ,,, At the other end of the vapor pressure spectrum, one finds pentaerythritol tetranitrate (PETN) − and 1,3,5-trinitroperhydro-1,3,5-triazine (RDX) , with vapor pressures in the range of 10 –9 –10 –10 Torr at room temperature. Thus, trace detection of most explosives is limited to their solid particle form.…”

Section: Introductionmentioning

confidence: 99%

Adhesion of Standard Explosive Particles to Model Surfaces

et al. 2012

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The adhesion of explosive particles to substrates with tailored chemical nature was analyzed by atomic force microscopy (AFM). Four different explosives were studied: TNT, RDX, HMX, and PETN. Two types of measurements were performed: in the first, a self-assembled monolayer (SAM) with different end groups was deposited on the tip and used to measure adhesion forces to an explosive particle surface. In the second type of experiment, the explosive particle was glued to the cantilever, and its adhesion force to a SAM-covered gold-plated glass substrate was measured. All experiments were performed both in ambient air and under water. The study shows that −OH and −C6H5 end groups lead to increased adhesion. In addition, we found that capillary forces have significantly contributed to the adhesion of explosive particles.

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Section: Introductionmentioning

confidence: 99%

Adhesion of Standard Explosive Particles to Model Surfaces

et al. 2012

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“…We had previously validated this IMDA approach to the tetrasubstituted tetrahydrofuran core of the cembranoids. 11j–m A fortuitous result noted during these studies was that upon formation of the desired ( E )-enoate for the Diels-Alder reaction, the cycloaddition proceeded rapidly, often spontaneously at room temperature. Gratifyingly, upon treatment with (acetylmethylene)triphenylphosphorane, 17 the crude aldehyde underwent an exo -selective Diels-Alder reaction to result in a single diastereomer ( 5 ).…”

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confidence: 99%

“…We have previously disclosed an asymmetric aldol−ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles 10 and demonstrated its utility in the total synthesis of multiple medium ring ether-containing natural products. 11 …”

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Total Syntheses of (+)-Vigulariol and (−)-Sclerophytin A

Crimmins

Stauffer

2011

Org. Lett.

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The total synthesis of (+)-vigulariol and (−)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.

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“…To properly functionalize the G ring, we had originally reported6b,d the use of the Crabtree catalyst20 under a hydrogen atmosphere for the hydrogenation of the endocyclic olefin. However, upon scale up, these conditions led to a somewhat disappointing 70 % yield of the desired oxocanes 105 , with loss of the PMB protecting group and epimerization at C26 by alkene isomerization accounting for undesirable portions of the mass balance.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits

Crimmins

Ellis

Emmitte

et al. 2009

Chemistry A European J

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Brevetoxin A is a decacyclic ladder toxin that possesses five-,six-, seven-, eight-, and nine-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings predicated upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the convergent completion of brevetoxin A.

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Enantioselective Synthesis of the G-Ring of Brevetoxin A

Cited by 18 publications

References 5 publications

Adhesion of Standard Explosive Particles to Model Surfaces

Adhesion of Standard Explosive Particles to Model Surfaces

Total Syntheses of (+)-Vigulariol and (−)-Sclerophytin A

Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits

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