A short convergent synthesis of the [3.2.1]dioxabicyclooctane subunit of sorangicin A via regioselective epoxide opening

Raghavan, Sadagopan; Nyalata, Satyanarayana

doi:10.1016/j.tet.2018.01.036

Cited by 5 publications

(3 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We disclosed earlier the synthesis of the C1–C15 subunit by Au(I)-catalyzed cyclization of an allenol and a short stereoselective synthesis of the C30–C37 subunit . Herein, we describe three different approaches to create the C25 stereogenic center of the C20–C29 subunit and its union with the C30–C37 subunit by a cross-metathesis reaction.…”

mentioning

confidence: 99%

“…With the C20–C29 subunit being available, further elaboration to the C20–C37 fragment was explored. The requisite alkene 37 was readily synthesized from compound 34 by a three-step sequence. Thus, deprotection of the PMB-ether furnished alcohol 35 .…”

mentioning

confidence: 99%

“…5 We disclosed earlier the synthesis of the C1−C15 subunit by Au(I)-catalyzed cyclization of an allenol 6 and a short stereoselective synthesis of the C30−C37 subunit. 7 Herein, we describe three different approaches to create the C25 stereogenic center of the C20−C29 subunit and its union with the C30−C37 subunit by a cross-metathesis reaction. Our initial approach to subunit 2 consisted of NHC-catalyzed boron-conjugate addition to unsaturated ketone 3 to create the C25 stereocenter, followed by reductive deoxygenation of a hemiketal to construct the C23 stereocenter.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Nyalata

Raghavan

2019

Org. Lett.

Self Cite

View full text Add to dashboard Cite

A convergent stereoselective route to the C16–C37 fragment of sorangicin A is disclosed using an α-chloro sulfide for C–C bond formation. The key intermediate, an α,β-unsaturated ketone, is revealed by a [2,3] sigmatropic rearrangement of a propargylic sulfoxide. Three disparate approaches are detailed to create the C25 carbinol stereocenter. The cis-2,6-disubstitution of the THP ring is secured by ionic hydrogenation. A cross-metathesis reaction and Julia–Kocienski olefination furnish the C16–C37 fragment of sorangicin A.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Nyalata

Raghavan

2019

Org. Lett.

Self Cite

View full text Add to dashboard Cite

show abstract

Three-Membered Ring Systems

Russel

2020

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

Six-Membered Ring Systems: With O and/or S Atoms

Santos¹,

Silva²

2020

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). NoticesKnowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

show abstract

A short convergent synthesis of the [3.2.1]dioxabicyclooctane subunit of sorangicin A via regioselective epoxide opening

Cited by 5 publications

References 28 publications

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Three-Membered Ring Systems

Six-Membered Ring Systems: With O and/or S Atoms

Contact Info

Product

Resources

About