Steroid total synthesis

Zeelen, F. J.

doi:10.1039/np9941100607

Cited by 53 publications

(21 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In order to exploit the potential applications of this method in synthetic chemistry, we chose (+)-estrone as a target. This molecule plays a key role in steroidogenesis20 and chemical synthesis of steroids 7,21,22. We followed Corey's route,9 as well as List's route,23 to synthesize Torgov's 1,3-diketone24 in a sub-gram scale.…”

Section: Resultsmentioning

confidence: 99%

Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

2019

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

2019

View full text Add to dashboard Cite

show abstract

“…Given this standing in medicinal chemistry, it is perhaps surprising that tetracyclic terpenoids persist as significant challenges for de novo synthesis. While numerous achievements have described synthetic forging of members of the broad class 7–13 , and the scientific advances central to such triumphs in natural product total synthesis have had a profound impact on the evolution of organic chemistry as a discipline, it remains the case that investigation of structure–activity relationships and production of active pharmaceutical ingredients (APIs) based on tetracyclic terpenoids typically proceed by derivatization of readily available natural products (a synthesis activity otherwise known as semisynthesis) 12 .…”

Section: Introductionmentioning

confidence: 99%

A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ

et al. 2019

View full text Add to dashboard Cite

Natural product and natural product-like molecules continue to be important for the development of pharmaceutical agents, as molecules in this class play a vital role in the pipeline for new therapeutics. Among these, tetracyclic terpenoids are privileged, with >100 being FDA-approved drugs. Despite this significant pharmaceutical success, there remain considerable limitations to broad medicinal exploitation of the class due to lingering scientific challenges associated with compound availability. Here, we report a concise asymmetric route to forging natural and unnatural (enantiomeric) C19 and C20 tetracyclic terpenoid skeletons suitable to drive medicinal exploration. While efforts have been focused on establishing the chemical science, early investigations reveal that the emerging chemical technology can deliver compositions of matter that are potent and selective agonists of the estrogen receptor beta, and that are selectively cytotoxic in two different glioblastoma cell lines (U251 and U87).

show abstract

“…Since the first total synthesis of equilenin in 1939 by Bachmann et al, [1] numerous synthetic approaches to obtain the tetracyclic structure of steroids have been developed, [2] many of them relying on biomimetic cyclizations of polyolefins, [3] cycloadditions, [4Ϫ8] or transition metal-catalyzed cyclizations of alkenes and alkynes. Since the first total synthesis of equilenin in 1939 by Bachmann et al, [1] numerous synthetic approaches to obtain the tetracyclic structure of steroids have been developed, [2] many of them relying on biomimetic cyclizations of polyolefins, [3] cycloadditions, [4Ϫ8] or transition metal-catalyzed cyclizations of alkenes and alkynes.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Novel 19-Nor-Steroids by a Double Heck Reaction

Tietze

Petersen

2001

Eur. J. Org. Chem.

View full text Add to dashboard Cite

Keywords: Cycloadditions / Ketones / Palladium / Steroids / CatalysisThe estrane 4 was synthesized by two successive Heck reactions starting from enantiopure 2 and the cyclohexenone 5, which contains a (Z)-bromovinyl group. The first intermolecular Pd-catalyzed reaction leads to 10 in a highly regioand diastereoselective manner. Transformation of the enone [a] Georg-August-Universität Göttingen, 1619 10 to give the corresponding enol triflate 14 followed by an intramolecular Heck reaction affords the cyclized product 4 with an unusual cis-junction of the rings B and C in high yield.

show abstract

Steroid total synthesis

Cited by 53 publications

References 52 publications

Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ

Stereoselective Synthesis of Novel 19-Nor-Steroids by a Double Heck Reaction

Contact Info

Product

Resources

About