Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777

Supplementary material for: [https://doi.org/10.1002/anie.201510777]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2048

Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C

During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (-)-atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors

Synthetic studies towards (+)-rauvomine B and other macroline/sarpagine alkaloids

Indole alkaloid (+)-rauvomine B1 contains cyclopropane ring incorporated in the unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this compound a challenging synthetic task. Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic intermediate, which could be efficiently prepared from commercially available N-Boc-(S)- tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate, via unified strategy

Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C

During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (-)-atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors

Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777

Supplementary material for: [https://doi.org/10.1002/anie.201510777]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2048

Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497

Supplementary material for: [https://doi.org/10.1002/chem.201900497]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2869]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/2874

Synthetic studies towards (+)-rauvomine B and other macroline/sarpagine alkaloids

Indole alkaloid (+)-rauvomine B1 contains cyclopropane ring incorporated in the unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this compound a challenging synthetic task. Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic intermediate, which could be efficiently prepared from commercially available N-Boc-(S)-tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate,via unified strategy.Abstract: [https://cherry.chem.bg.ac.rs/handle/123456789/5934

Supplementary data for article: Bihelović, F.; Karadžić, I.; Matović, R.; Saičić, R. Total Synthesis and Biological Evaluation of (-)-Atrop-Abyssomicin C. Organic and Biomolecular Chemistry 2013, 11 (33), 5413–5424. https://doi.org/10.1039/c3ob40692j

Supplementary material for: [https://doi.org/10.1039/c3ob40692j]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1388

A copper carbenoid insertion/Horner-Wadsworth-Emmons reaction as a new method for the synthesis (+)-alstonlarsine A tricyclic core

Jedan od ključnih koraka u okviru planirane totalne sinteze (+)-alstonlarsina A1 je intramolekulska Horner-Wadsworth-Emmons-ova (HWE) reakcija za zatvaranje cikloheptenskog prstena. Nedavno izolovani monoterpenski indolski alkaloid (+)- alstonlarsin A poseduje jedinstvenu kavezastu strukturu, kao i biološki interesantnu osobinu da se ponaša kao inhibitor DRAK2 enzima. Stoga je razvijena nova metodologija za funkcionalizaciju indola u položaju 2, kako bi se sintetisao odgovarajući 2- fosfonoacetatni indolski prekursor. Ova metodologija se zasniva na efikasnoj intramolekulskoj bakar-karbenoidnoj inserciji, čime je omogućena kasnija HWE reakcija i dobijanje kondenzovanih indolskih derivata sa kondenzovanim petočlanim, šestočlanim, sedmočlanim i osmočlanim prstenom.One of the key steps in our efforts toward the total synthesis of (+)-alstonlarsine A1 – a recently isolated monoterpenoid indole alkaloid possessing a unique cage-shaped structure and acting as Drak2 inhibitor – was an intramolecular Horner-Wadsworth-Emmons (HWE) reaction for the formation of the cycloheptene ring. To achieve this transformation, a new methodology for indole C-2 functionalization was developed aiming to synthesize the 2-phosphonoacetate indole precursor. The represented methodology relied on an efficient intermolecular copper carbenoid insertion, thus allowing a subsequent formation of indole derivatives with condensed 5-, 6-, 7- and 8-membered rings via HWE reaction.Poster: [https://cherry.chem.bg.ac.rs/handle/123456789/5930

Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A

Two new analogues of alstoscholarisine A, containing a phenyl or butyl substituent at the C-19 position, have been prepared in racemic form from the known skatole derivative. The syntheses of these compounds were accomplished in 13 steps, with a late-stage formation of the C-19 stereocenter. These derivatives are expected to have significantly changed biological activity, compared to alstoscholarisine A – a potent neuroactive natural product