Synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: a silicon mediated total synthesis of (+)-carpamic acid

Singh, Rekha; Ghosh, Sunil K.

doi:10.1016/s0040-4039(02)01853-1

Cited by 34 publications

(15 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ghosh and co‐worker [51] in 2002 reported the diastereoselective synthesis of (+)‐carpamic acid from symmetric 3‐[dimethyl(phenyl)silyl]glutaric anhydride 130 . The key steps involved are the desymmetrisation of 130 with oxazolidinone 131 , silicon directed highly stereoselective enolate methylation, and silicon facilitated Curtius reaction.…”

Section: (+)‐Carpamic Acidmentioning

confidence: 99%

Use of Non‐Aromatic Hydrophobic α‐Amino Acids (α‐AA) and Non‐Amino Acid Derived Synthons: Comparative Studies Towards Total Syntheses of Selected Bioactive Natural Alkaloids

et al. 2022

View full text Add to dashboard Cite

the total synthesis of selected natural alkaloids have been compared based on atom economy, overall chemical yield, stereoselectivity and sustainability with cost effective manner by using inexpensive commercially available starting materials but the source of chiral pool mainly α-amino acids to target natural alkaloids in chiral synthesis will be playing an important role. In selected cases of alkaloids synthesized from non-amino acid route, an external chiral source of induction like metal and organometallic catalysts to generate chirality in the molecule are used.

show abstract

Section: (+)‐Carpamic Acidmentioning

confidence: 99%

Use of Non‐Aromatic Hydrophobic α‐Amino Acids (α‐AA) and Non‐Amino Acid Derived Synthons: Comparative Studies Towards Total Syntheses of Selected Bioactive Natural Alkaloids

et al. 2022

View full text Add to dashboard Cite

show abstract

“…97 Azimine (58) 98 and carpaine (59), 99,100 were initially isolated from Azima tetracantha L. and Carica papaya L., respectively and being the new family of macrocyclic dilactones comprising a 2,3,6-trisubstituted piperidine scaffold, and carpaine is reported to show a wide scope of biological activities as well as antitumor activity at even low concentrations. 101 Synthetic potency in this eld has led into the preparation of azimic acid 102,103 and carpamic acid 104,105 both as racemate and enantiomeric forms. However, there has been only a single report concerning with the synthesis of the macrocyclic dilactone family of alkaloid, carpaine (59), developed, and present jointly by Corey and Nicolaou.…”

Section: Intramolecular Hetero Diels-alder (Imhda) Reactionmentioning

confidence: 99%

Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

et al. 2015

View full text Add to dashboard Cite

show abstract

“…(+)-Spectaline (17) has been targeted by the groups of Ham and Trost. Ham's approach (Scheme 6) [13] commenced from L-serinol 49, which was smoothly transformed in four steps to trans-oxazoline 51, exploiting the chemistry of -allyl Pd complexes.…”

Section: Reductive Aminationmentioning

confidence: 99%

“…Ghosh exploited the chemistry of organosilicon compounds for his synthesis of (+)-Carpamic acid (67) [17]. Thus employing chiral auxiliary (CA) 68 the symmetric anhydride 69 was converted to homochiral intermediate 70, which was elaborated to aminoketone 71 (R = CH 2 (CH 2 ) 7 OBn; Scheme 10).…”

Section: Reductive Aminationmentioning

confidence: 99%

Stereoselective Syntheses of 2,6-disubstituted Piperidin-3-oles (alkaloid lipids)

Koulocheri¹,

Pitsinos²,

Haroutounian

2008

COC

View full text Add to dashboard Cite

Alkaloid lipids comprise a class of natural compounds with significant biological activities of medicinal interest. Their structural framework consists of a 2,6-disubstituted-3-piperidinol moiety (polar head group) and a lipid tail. Representative examples of alkaloid lipids are (+)-Cassine, ( )-Prosophylline, ( )-Prosopinine, ( )-Spectalline.Many synthetic strategies have been developed for the efficient stereoselective synthesis of various natural alkaloid lipids and their synthetic analogues. This mini-review focuses on the most successful approaches published during the new millennium. The synthetic strategies are grouped in two main sections, depending on whether the lipophilic side chain is introduced before ("early") or after ("late") piperidine ring formation. These sections are further organised based on the key ring forming reaction/strategy employed.For the strategies that opt to introduce the lipophilic side chain early on the synthetic sequence, the intramolecular reductive amination, either with or without isolation of the intermediate imine/enamine, constitutes one of the most popular methods for constructing the piperidine ring followed closely by approaches based on the intramolecular alkylation of suitable amine derivatives. Olefin ring closing metathesis and intramolecular hetero-Diels-Alder reactions have also been exploited to secure the azaheterocycle.The intramolecular alkylation of an amine or the, retrosynthetically related, intramolecular amine addition to an olefin have also been employed as key ring-forming reactions by syntheses that adopt the more convergent approach of introducing the side chain on a preformed heterocycle. In this regard the introduction of the side chain via alkylation of pyridinium salts, alkylation of a lactam (2-piperidone) or glutarimide derivatives have been investigated. Several groups have also exploited the oxidative cyclization of -furylamines to prepare 2-dihydropyridones as a convenient scaffold for the late introduction of the lipid tail.In some cases, carbohydrates and aminoacids were used (either as starting materials or as chiral auxiliaries) for the enantioselective synthesis of alkaloid lipids. Enzymatic or chemical (Jacobsen's epoxide hydrolysis protocol) resolutions of racemic starting materials and Sharpless asymmetric epoxidation, dihydroxylation or aminohydroxylation of olefins have also been utilized.Finally, it is noteworthy that in several cases, apart from the Witting reaction and the use of Grignard reagents, olefin cross-metathesis has also been successfully employed for the introduction of the lipid side chain.

show abstract

Synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: a silicon mediated total synthesis of (+)-carpamic acid

Cited by 34 publications

References 37 publications

Use of Non‐Aromatic Hydrophobic α‐Amino Acids (α‐AA) and Non‐Amino Acid Derived Synthons: Comparative Studies Towards Total Syntheses of Selected Bioactive Natural Alkaloids

Use of Non‐Aromatic Hydrophobic α‐Amino Acids (α‐AA) and Non‐Amino Acid Derived Synthons: Comparative Studies Towards Total Syntheses of Selected Bioactive Natural Alkaloids

Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

Stereoselective Syntheses of 2,6-disubstituted Piperidin-3-oles (alkaloid lipids)

Contact Info

Product

Resources

About